Category: 14613-37-7

Wohl, A. published the artcileArecolone and N-methyl-ω-amina-β-pipecoline, Recommanded Product: (1-Methylpiperidin-3-yl)methanamine, the publication is Justus Liebigs Annalen der Chemie (1924), 139-49, database is CAplus.

Condensation of (EtO)₂CHCH₂CH₂NH₂ and HCHO gives an anhydro-base, [CH₂:NCH₂CH₂CH(OEt)₂]_n, oil which decomposes on distilling in vacuo and reduces Fehling solution and NH₄OH-AgNO₃. A modification of Blaise and Maire’s method for CH₂:CHAc (C. A. 2, 1824) is given, the yields being 25-35%. The residue, treated with AcCl, gives the compound, C₉H₁₄O₅, m. 85°. CH₂: CHAc does not appear to condense with (EtO)₂CHCH₂NH₂ to give a definite compound With (EtO)₂CHCH₂CH₂NHMe, there results the compound, (EtO)₂CHCH₂CH₂NMeCH₂CH₂Ac, light yellow oil, which cannot be distd, in vacuum but with concentrated HCl in a cooling mixture it yields 40-60% of the HCl salt, m. 204°, of arecolone (N-methyl-Δ³-tetrahydropyridine β-Me ketone), light yellow oil, b_0.01 80-2°, reduces acid KMnO₄ in the cold. HBr salt, m. 223°. Semicarbazone, m. 219° (decomposition); HCl salt, m. 233°. Arecaidine aldehyde oxime, m. 130°. Reduction with Na-Hg gives 50% of N-methyl-ω-amino-β-pipecoline, b₁₂ 116-8°; Bz derivative, m. 161-2°.

Justus Liebigs Annalen der Chemie published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C18H35NO, Recommanded Product: (1-Methylpiperidin-3-yl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Deguchi, Yoshio published the artcilePiperidine derivatives, Computed Properties of 14613-37-7, the publication is Iyaku Shigen Kenkyusho Nempo (1956), 17-22, database is CAplus.

Dialkylureido-N-methylpiperidines and dialkylureidomethyl-N-methylpiperidines were prepared Pyridine-3-carboxylic acid amide (10 g.) is refluxed with 17.5 g. MeI and 30 cc. MeOH for 5 hrs., evaporated, the residue is dissolved in 30 cc. H₂O, warmed with freshly prepared AgCl (prepared from 20 g. AgNO₃ and 7 g. NaCl) for 3 hrs., and filtered. The filtrate is decolorized with active C and then catalytically reduced with 0.1 g. PtO₂ to give 85% N-methylpiperidine-3-carboxamide (I); hydrochloride m. 232° (alc.). Similarly was prepared N-methylpiperidine-4-carboxamide; hydrochloride, hygroscopic. A mixture of 7 g. I and 7 g. P₂O₅ is heated at 160-180° for 3 hrs., cooled, dissolved in 50 cc. H₂O with warming, neutralized with K₂CO₃, salted out, and the separated oil extracted with AcOEt to give 80% 3-cyano-N-methylpiperidine (II), b₂₀ 95-6°. Similarly was prepared 4-cyano-N-methylpiperidine, b₂₁ 97°. Into a cooled mixture of 1.3 g. LiAlH₄ and 150 cc. Et₂O is dropped a solution of 5.0 g. II in 50 cc. Et₂O during 90 min., the mixture stirred 1 hr., refluxed 30 min., 15 cc. H₂O added to decompose excess LiAlH₄, and filtered. The filtrate is dried with KOH, evaporated, and distilled in vacuo to give 90% 3-aminomethyl-N-methylpiperidine (III), b₂₀ 81-2°; dipicrate m. 231° (decomposition). Similarly was prepared 4-aminomethyl-N-methylpiperidine (IV), b₂₀ 80-1°; dipicrate m. 236° (decomposition). To a mixture of 32 g. KOH, 6.4 g. Br, and 400 cc. H₂O is dropped an aqueous solution of 5.7 g. I under ice cooling, then warmed at 70° for 1 hr., alkalized with KOH, distilled with steam, and the distilled solution treated with diluted HCl, concentrated in vacuo, alkalized with KOH, extracted with Et₂O, and the extract evaporated and distilled in vacuo to give 65% 3-amino-N-methylpiperidine (V), b₄₃ 74-5°; dipicrate m. 227° (decomposition). Similarly was prepared 4-amino-N-methyl-piperidine (VI), b₃₅ 70-1°; dipicrate m. 263° (decomposition). A mixture of 0.6 mole Me₂NH and 200 cc. PhMe is dropped into 50% phosgene-PhMe, refluxed 1 hr., and distilled in vacuo to give 40% dimethylcarbamoyl chloride (VII), b_55-60 85-8°. Similarly was prepared diethylcarbamoyl chloride (VIII), b_17-20 80°. A mixture of 2 moles III and 1 mole VII in Et₂O is kept at room temperature 1.5 hrs., refluxed 10 min., cooled, and filtered. The filtrate is evaporated and chromatographed using alumina to give 3-dimethylureidomethyl-N-methyl-piperidine, needles (petr.-ether), m. 66-9° (hygroscopic). Similarly were prepared following IX (starting materials, position of substituent, n, R, appearance, and m.p. given): III and VIII, 3, 1, Et, sirupy, -; IV and VII, 4, 1, Me, needles (hygroscopic), 40-4° (hydrochloride m. 230°); IV and VIII, 4, 1, Et, columns, 66-8°; V and VIII, 3, 0, Me, needles, 110-12°; V and VIII, 3, 1, Et, sirupy, (picrolonate m. 195-7°); VI and VII, 4, 0, Me, flakes, 138-9°; VI and VIII, 4, 0, Et, needles, 89-90°.

Iyaku Shigen Kenkyusho Nempo published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Computed Properties of 14613-37-7.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Hutchins, Robert O. published the artcileConformational analysis of phosphorus heterocycles. Proton and phosphorus-31 nuclear magnetic resonance study of N,N’-dimethyl-(2R)-2-phospha-1,3-diazacyclohexanes, Safety of (1-Methylpiperidin-3-yl)methanamine, the publication is Journal of the American Chemical Society (1972), 94(26), 9151-8, database is CAplus.

An examination of a series of N,N’-dimethyl-(2R)-2-phospha- and N,N’-5,5-tetramethyl-(2R)-2-phospha-1,3-diazacyclohexanes (R = Cl, OMe, Et, Me, Ph) by H and 31P NMR spectra reveals predominantly single chair conformations, probably with diequatorial N-methyl groups. The P-N-C-H coupling constants are quite variant with the P substituent and suggest that the N hybridization, and consequently the flattening of the rings, is very dependent upon the electronegativity of the P substituent. The stereochemistry of the P substituents is discussed.

Journal of the American Chemical Society published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Safety of (1-Methylpiperidin-3-yl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem