Tag: 171.24

Synthesis of piperidinemethanols. I. Synthesis of 伪,伪-diphenyl- or 伪-phenyl-伪-thienyl-l-methylpiperidine-methanol was written by Sugimoto, Norio;Kugita, Hiroshi. And the article was included in Yakugaku Zasshi in 1953.Application of 30727-18-5 This article mentions the following:

A 2-BzC₅H₄N (13.5 g.), 14 g. MeI, and 35 ml. MeOH heated 3 hrs. at 100掳 in a sealed tube and the MeOH removed give sirupy 2-BzC₅H₄N.MeI; this with AgCl gives 16 g. sirupy 2-BzC₅H₄N. MeCl; catalytic reduction of this with 0.3 g. PtO₂ in 70 ml. alc., addition of a small amount of water, making alk. with K₂CO₃, extraction with Et₂O, and distillation, gives 11 g. liquid, b₁₀ 153-62掳, the liquid, in a small amount of Me₂CO, treated with 13.5 g. picric acid, and the picrate fractionally crystallized from MeOH and decomposed with 25% NH₄OH gives 2.1 g. 2-PhCH(OH)C₅H₉NMe (IA), b_5.5 140-3掳, plates, m. 61-2掳 (picrate, m. 201-4掳); 3.8 g. isomer (IB) of IA, b_6.6 143-6掳 (picrate, m. 158-63掳); 0.3 g. m. 140掳 (picrate, m. 170-2掳); and 2.3 g. (IC), b_5.5 138-45掳 (picrate, sirupy; picrolonate, m. 160-3掳). IB (3.8 g.) and 60 ml. AcOH at 50-60掳treated dropwise with 1.3 g. CrO₃ in 11 ml. 90% AcOH, heated 30 min. at 80掳, part of AcOH removed in vacuo, the residue neutralized with NaOH, the oily layer extracted with Et₂O, and the extract distilled give 80% 2-BzC₅H₉NMe (II), b_5.5 136-9掳 (picrolonate, rhombic, m. 160-3掳); similarly, IA gives II, b_4.5 135掳 (picrolonate, m. 160-3掳). IA (1 g.) distilled in vacuo, and the fraction b_3.5 128.5-9.5掳 treated with picric acid gives 1.9 g. picrate, m. 206-7掳; the mother liquor treated with NH₄OH, and extracted with Et₂O, yields a picrolonate of II, m. 160-2掳. On catalytic reduction IC absorbed 1 mole H and gave a picrate, m. 204-6掳 (which lowers the m.p. of IA picrate). On catalytic reduction in 100 ml. EtOH with 0.5 g. PtO₂ 32.6 g. sirupy 3-PhCH(OH)C₅H₄N.MeCl absorbed 10 1. H (3 moles); removing the EtOH, neutralizing with K₂CO₃, extracting with Et₂O, and distilling gave 3-PhCH(OH)C₅H₉NMe (IIIA), columns, m. 125-7掳, an isomer (IIIB) of IIIA, rhombic, m. 116-17掳 (yield of IIIA and IIIB combined 10.5 g.), 5.5 g. 3-BzC₅H₉NMe (IV) (picrate, m. 193-5掳), and 7.1 g. liquid (picrate, m. 154.5-5掳). A mixture (4 g.) of IIIA and IIIB in 80 ml. AcOH at 50掳 treated dropwise with 1.3 g. CrO₃ in 6 ml. 80% AcOH, heated 1 hr. at 90掳, and the product treated as for II gives 3.5 g. (87.5%) IV, b₂ 140-4掳; picrate 194-6掳 (from dioxane). 4-BzC₅H₄N (9.1 g.), 14.2 g. MeI, and 50 ml. MeOH, heated 2 hrs. on a water bath, the MeOH removed, and the residue washed with Me₂CO and recrystallized from alc. give 13 g. 4-BzC₅H₄N.MeI (V), m. 80-180掳, which on catalytic reduction in 80 ml. MeOH with 0.3 g. PtO₂ absorbed 4 moles H and gave 8 g. 4-PhCH(OH)C₆H₉NMe (VI). m. 157-9掳 (from dilute alc.); 3 g. VI and 1 g. CrO₃ in AcOH, heated 20 min. at 90掳, gave 2.1 g. (70%) 4-BzC₅H₉NMe (VII), b₅ 157-9掳; picrate, m. 200.5-2掳. II (1.35 g.) in 10 ml. dry Et₂O added to PhMgBr (2.3 g. PhBr, 0.35 g. Mg, and 10 ml. Et₂O), the mixture refluxed 45 min., decomposed with NH₄Cl, and the product extracted with Et₂O, taken up in 10% HCl, neutralized with K₂CO₃, extracted with Et₂O, and distilled gave 0.6 g. 2-RC₅H₉NMe [VIII, R = Ph₂C(OH) (IX)], columns, m. 88.5-9.5掳; similarly, IV yielded 72.3% 3-RC₅H₉NMe (X, R = IX) needles, m. 147-8掳 (from dilute alc.); VII yielded 46.4% 4-RC₅H₉NMe (XI, R = IX), granules, m. 134-6掳 (from petr. ether). 2-(Ph₂CH(OH)C₅H₄N.MeCl, decompose 227掳, (6 g.) on catalytic reduction in 100 ml. alc. with 0.2 g. PtO₂ for 3 hrs. absorbed 3 moles H; the product filtered, the alc. in the filtrate removed, and the residue taken up with water, made alk. with K₂CO₃, and extracted with Et₂O gave 5.3 g. VIII, m. 89-90掳 (from petr. ether). II (2.5 g.) in 30 ml. dry Et₂O added a Grignard reagent from 3 g. 2-bromothiophene, 0.45 g. Mg, and 30 ml. Et₂O, the mixture refluxed 3 hrs., and decomposed with aqueous NH₄Cl, gave 1.6 g. 2-PhCR(OH)C₅H₉NMe (XII, R = 2-thienyl), needles, m. 93-4掳 (from dilute alc.); similarly are obtained 67.5% 3-PhCR(OH)C₅H₉NMe, needles, m. 142-3掳, and 15.4% 4-PhCR(OH)C₅H₉NMe, prisms, m. 147-8掳 (from petr. ether). In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Application of 30727-18-5).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Application of 30727-18-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Benzotriazole-Mediated Stereoselective Olefination of Carboxylic Esters: Transformation of 伪-Amino Acid Esters into Chiral Allylamines was written by Katritzky, Alan R.;Cheng, Dai;Li, Jianqing. And the article was included in Journal of Organic Chemistry in 1998.Category: piperidines This article mentions the following:

Diastereoselective trans-olefinations of carboxylic esters have been accomplished using benzylic or allylic benzotriazole derivatives to prepare 伪-(benzotriazol-1-yl) ketones, subsequent reduction of the ketones, and finally low-valent titanium-effected dehydroxybenzotriazolylation. In a similar manner, N-protected 伪-amino acid esters give allylamines with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed. In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Category: piperidines).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of piperidinemethanols. I. Synthesis of α,α-diphenyl- or α-phenyl-α-thienyl-l-methylpiperidine-methanol was written by Sugimoto, Norio;Kugita, Hiroshi. And the article was included in Yakugaku Zasshi in 1953.Application of 30727-18-5 This article mentions the following:

A 2-BzC₅H₄N (13.5 g.), 14 g. MeI, and 35 ml. MeOH heated 3 hrs. at 100° in a sealed tube and the MeOH removed give sirupy 2-BzC₅H₄N.MeI; this with AgCl gives 16 g. sirupy 2-BzC₅H₄N. MeCl; catalytic reduction of this with 0.3 g. PtO₂ in 70 ml. alc., addition of a small amount of water, making alk. with K₂CO₃, extraction with Et₂O, and distillation, gives 11 g. liquid, b₁₀ 153-62°, the liquid, in a small amount of Me₂CO, treated with 13.5 g. picric acid, and the picrate fractionally crystallized from MeOH and decomposed with 25% NH₄OH gives 2.1 g. 2-PhCH(OH)C₅H₉NMe (IA), b_5.5 140-3°, plates, m. 61-2° (picrate, m. 201-4°); 3.8 g. isomer (IB) of IA, b_6.6 143-6° (picrate, m. 158-63°); 0.3 g. m. 140° (picrate, m. 170-2°); and 2.3 g. (IC), b_5.5 138-45° (picrate, sirupy; picrolonate, m. 160-3°). IB (3.8 g.) and 60 ml. AcOH at 50-60°treated dropwise with 1.3 g. CrO₃ in 11 ml. 90% AcOH, heated 30 min. at 80°, part of AcOH removed in vacuo, the residue neutralized with NaOH, the oily layer extracted with Et₂O, and the extract distilled give 80% 2-BzC₅H₉NMe (II), b_5.5 136-9° (picrolonate, rhombic, m. 160-3°); similarly, IA gives II, b_4.5 135° (picrolonate, m. 160-3°). IA (1 g.) distilled in vacuo, and the fraction b_3.5 128.5-9.5° treated with picric acid gives 1.9 g. picrate, m. 206-7°; the mother liquor treated with NH₄OH, and extracted with Et₂O, yields a picrolonate of II, m. 160-2°. On catalytic reduction IC absorbed 1 mole H and gave a picrate, m. 204-6° (which lowers the m.p. of IA picrate). On catalytic reduction in 100 ml. EtOH with 0.5 g. PtO₂ 32.6 g. sirupy 3-PhCH(OH)C₅H₄N.MeCl absorbed 10 1. H (3 moles); removing the EtOH, neutralizing with K₂CO₃, extracting with Et₂O, and distilling gave 3-PhCH(OH)C₅H₉NMe (IIIA), columns, m. 125-7°, an isomer (IIIB) of IIIA, rhombic, m. 116-17° (yield of IIIA and IIIB combined 10.5 g.), 5.5 g. 3-BzC₅H₉NMe (IV) (picrate, m. 193-5°), and 7.1 g. liquid (picrate, m. 154.5-5°). A mixture (4 g.) of IIIA and IIIB in 80 ml. AcOH at 50° treated dropwise with 1.3 g. CrO₃ in 6 ml. 80% AcOH, heated 1 hr. at 90°, and the product treated as for II gives 3.5 g. (87.5%) IV, b₂ 140-4°; picrate 194-6° (from dioxane). 4-BzC₅H₄N (9.1 g.), 14.2 g. MeI, and 50 ml. MeOH, heated 2 hrs. on a water bath, the MeOH removed, and the residue washed with Me₂CO and recrystallized from alc. give 13 g. 4-BzC₅H₄N.MeI (V), m. 80-180°, which on catalytic reduction in 80 ml. MeOH with 0.3 g. PtO₂ absorbed 4 moles H and gave 8 g. 4-PhCH(OH)C₆H₉NMe (VI). m. 157-9° (from dilute alc.); 3 g. VI and 1 g. CrO₃ in AcOH, heated 20 min. at 90°, gave 2.1 g. (70%) 4-BzC₅H₉NMe (VII), b₅ 157-9°; picrate, m. 200.5-2°. II (1.35 g.) in 10 ml. dry Et₂O added to PhMgBr (2.3 g. PhBr, 0.35 g. Mg, and 10 ml. Et₂O), the mixture refluxed 45 min., decomposed with NH₄Cl, and the product extracted with Et₂O, taken up in 10% HCl, neutralized with K₂CO₃, extracted with Et₂O, and distilled gave 0.6 g. 2-RC₅H₉NMe [VIII, R = Ph₂C(OH) (IX)], columns, m. 88.5-9.5°; similarly, IV yielded 72.3% 3-RC₅H₉NMe (X, R = IX) needles, m. 147-8° (from dilute alc.); VII yielded 46.4% 4-RC₅H₉NMe (XI, R = IX), granules, m. 134-6° (from petr. ether). 2-(Ph₂CH(OH)C₅H₄N.MeCl, decompose 227°, (6 g.) on catalytic reduction in 100 ml. alc. with 0.2 g. PtO₂ for 3 hrs. absorbed 3 moles H; the product filtered, the alc. in the filtrate removed, and the residue taken up with water, made alk. with K₂CO₃, and extracted with Et₂O gave 5.3 g. VIII, m. 89-90° (from petr. ether). II (2.5 g.) in 30 ml. dry Et₂O added a Grignard reagent from 3 g. 2-bromothiophene, 0.45 g. Mg, and 30 ml. Et₂O, the mixture refluxed 3 hrs., and decomposed with aqueous NH₄Cl, gave 1.6 g. 2-PhCR(OH)C₅H₉NMe (XII, R = 2-thienyl), needles, m. 93-4° (from dilute alc.); similarly are obtained 67.5% 3-PhCR(OH)C₅H₉NMe, needles, m. 142-3°, and 15.4% 4-PhCR(OH)C₅H₉NMe, prisms, m. 147-8° (from petr. ether). In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Application of 30727-18-5).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Application of 30727-18-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Benzotriazole-Mediated Stereoselective Olefination of Carboxylic Esters: Transformation of α-Amino Acid Esters into Chiral Allylamines was written by Katritzky, Alan R.;Cheng, Dai;Li, Jianqing. And the article was included in Journal of Organic Chemistry in 1998.Category: piperidines This article mentions the following:

Diastereoselective trans-olefinations of carboxylic esters have been accomplished using benzylic or allylic benzotriazole derivatives to prepare α-(benzotriazol-1-yl) ketones, subsequent reduction of the ketones, and finally low-valent titanium-effected dehydroxybenzotriazolylation. In a similar manner, N-protected α-amino acid esters give allylamines with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed. In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Category: piperidines).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of piperidinemethanols. I. Synthesis of α,α-diphenyl- or α-phenyl-α-thienyl-l-methylpiperidine-methanol was written by Sugimoto, Norio;Kugita, Hiroshi. And the article was included in Yakugaku Zasshi in 1953.Application of 30727-18-5 This article mentions the following:

A 2-BzC₅H₄N (13.5 g.), 14 g. MeI, and 35 ml. MeOH heated 3 hrs. at 100° in a sealed tube and the MeOH removed give sirupy 2-BzC₅H₄N.MeI; this with AgCl gives 16 g. sirupy 2-BzC₅H₄N. MeCl; catalytic reduction of this with 0.3 g. PtO₂ in 70 ml. alc., addition of a small amount of water, making alk. with K₂CO₃, extraction with Et₂O, and distillation, gives 11 g. liquid, b₁₀ 153-62°, the liquid, in a small amount of Me₂CO, treated with 13.5 g. picric acid, and the picrate fractionally crystallized from MeOH and decomposed with 25% NH₄OH gives 2.1 g. 2-PhCH(OH)C₅H₉NMe (IA), b_5.5 140-3°, plates, m. 61-2° (picrate, m. 201-4°); 3.8 g. isomer (IB) of IA, b_6.6 143-6° (picrate, m. 158-63°); 0.3 g. m. 140° (picrate, m. 170-2°); and 2.3 g. (IC), b_5.5 138-45° (picrate, sirupy; picrolonate, m. 160-3°). IB (3.8 g.) and 60 ml. AcOH at 50-60°treated dropwise with 1.3 g. CrO₃ in 11 ml. 90% AcOH, heated 30 min. at 80°, part of AcOH removed in vacuo, the residue neutralized with NaOH, the oily layer extracted with Et₂O, and the extract distilled give 80% 2-BzC₅H₉NMe (II), b_5.5 136-9° (picrolonate, rhombic, m. 160-3°); similarly, IA gives II, b_4.5 135° (picrolonate, m. 160-3°). IA (1 g.) distilled in vacuo, and the fraction b_3.5 128.5-9.5° treated with picric acid gives 1.9 g. picrate, m. 206-7°; the mother liquor treated with NH₄OH, and extracted with Et₂O, yields a picrolonate of II, m. 160-2°. On catalytic reduction IC absorbed 1 mole H and gave a picrate, m. 204-6° (which lowers the m.p. of IA picrate). On catalytic reduction in 100 ml. EtOH with 0.5 g. PtO₂ 32.6 g. sirupy 3-PhCH(OH)C₅H₄N.MeCl absorbed 10 1. H (3 moles); removing the EtOH, neutralizing with K₂CO₃, extracting with Et₂O, and distilling gave 3-PhCH(OH)C₅H₉NMe (IIIA), columns, m. 125-7°, an isomer (IIIB) of IIIA, rhombic, m. 116-17° (yield of IIIA and IIIB combined 10.5 g.), 5.5 g. 3-BzC₅H₉NMe (IV) (picrate, m. 193-5°), and 7.1 g. liquid (picrate, m. 154.5-5°). A mixture (4 g.) of IIIA and IIIB in 80 ml. AcOH at 50° treated dropwise with 1.3 g. CrO₃ in 6 ml. 80% AcOH, heated 1 hr. at 90°, and the product treated as for II gives 3.5 g. (87.5%) IV, b₂ 140-4°; picrate 194-6° (from dioxane). 4-BzC₅H₄N (9.1 g.), 14.2 g. MeI, and 50 ml. MeOH, heated 2 hrs. on a water bath, the MeOH removed, and the residue washed with Me₂CO and recrystallized from alc. give 13 g. 4-BzC₅H₄N.MeI (V), m. 80-180°, which on catalytic reduction in 80 ml. MeOH with 0.3 g. PtO₂ absorbed 4 moles H and gave 8 g. 4-PhCH(OH)C₆H₉NMe (VI). m. 157-9° (from dilute alc.); 3 g. VI and 1 g. CrO₃ in AcOH, heated 20 min. at 90°, gave 2.1 g. (70%) 4-BzC₅H₉NMe (VII), b₅ 157-9°; picrate, m. 200.5-2°. II (1.35 g.) in 10 ml. dry Et₂O added to PhMgBr (2.3 g. PhBr, 0.35 g. Mg, and 10 ml. Et₂O), the mixture refluxed 45 min., decomposed with NH₄Cl, and the product extracted with Et₂O, taken up in 10% HCl, neutralized with K₂CO₃, extracted with Et₂O, and distilled gave 0.6 g. 2-RC₅H₉NMe [VIII, R = Ph₂C(OH) (IX)], columns, m. 88.5-9.5°; similarly, IV yielded 72.3% 3-RC₅H₉NMe (X, R = IX) needles, m. 147-8° (from dilute alc.); VII yielded 46.4% 4-RC₅H₉NMe (XI, R = IX), granules, m. 134-6° (from petr. ether). 2-(Ph₂CH(OH)C₅H₄N.MeCl, decompose 227°, (6 g.) on catalytic reduction in 100 ml. alc. with 0.2 g. PtO₂ for 3 hrs. absorbed 3 moles H; the product filtered, the alc. in the filtrate removed, and the residue taken up with water, made alk. with K₂CO₃, and extracted with Et₂O gave 5.3 g. VIII, m. 89-90° (from petr. ether). II (2.5 g.) in 30 ml. dry Et₂O added a Grignard reagent from 3 g. 2-bromothiophene, 0.45 g. Mg, and 30 ml. Et₂O, the mixture refluxed 3 hrs., and decomposed with aqueous NH₄Cl, gave 1.6 g. 2-PhCR(OH)C₅H₉NMe (XII, R = 2-thienyl), needles, m. 93-4° (from dilute alc.); similarly are obtained 67.5% 3-PhCR(OH)C₅H₉NMe, needles, m. 142-3°, and 15.4% 4-PhCR(OH)C₅H₉NMe, prisms, m. 147-8° (from petr. ether). In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Application of 30727-18-5).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Application of 30727-18-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Benzotriazole-Mediated Stereoselective Olefination of Carboxylic Esters: Transformation of α-Amino Acid Esters into Chiral Allylamines was written by Katritzky, Alan R.;Cheng, Dai;Li, Jianqing. And the article was included in Journal of Organic Chemistry in 1998.Category: piperidines This article mentions the following:

Diastereoselective trans-olefinations of carboxylic esters have been accomplished using benzylic or allylic benzotriazole derivatives to prepare α-(benzotriazol-1-yl) ketones, subsequent reduction of the ketones, and finally low-valent titanium-effected dehydroxybenzotriazolylation. In a similar manner, N-protected α-amino acid esters give allylamines with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed. In the experiment, the researchers used many compounds, for example, Ethyl 1-methylpipecolinate (cas: 30727-18-5Category: piperidines).

Ethyl 1-methylpipecolinate (cas: 30727-18-5) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem