Vil’yams, V. V.’s team published research in Dokl., Rossiisk. Sel’skokhoz. Akad. in No. 99 | CAS: 14613-37-7

Dokl., Rossiisk. Sel’skokhoz. Akad. 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 C3H6O2, Formula: C7H16N2.

Vil’yams, V. V. published the artcileThe ring isomerization in some nitrogen-containing heterocyclic compounds. Synthesis of amino and hydroxy derivatives of β-methylpiperidine, Formula: C7H16N2, the publication is Dokl., Rossiisk. Sel’skokhoz. Akad. (1964), 553-7, database is CAplus.

The synthesis of 1-methyl-3-(aminomethyl)piperidine (I) and 3-piperidinylmethanol (II) was described. A mixture of 61 g. nicotinamide, 106.5 g. MeI, 200 ml. MeOH, and a trace of nicotinamide methiodide was refluxed 3 hrs., the solution evaporated in vacuo, the residue dissolved in 150 ml. H2O and boiled with freshly prepared AgCl (from 120 g. AgNO3 and 42 g. NaCl) for 5 hrs. The reaction mixture was filtered (charcoal) and hydrogenated over 0.4 g. PtO2 36 hrs. at 3.5-1.5 atm. to give 87% nipecotamide methochloride (III), m. 239°. III heated with an equal amount P2O5 5 hrs. at 180°, treated with hot H2O, neutralized with K2CO3, and extracted with AcOEt yielded 76% 1-methyl-3-cyanopiperidine (IV), b23 106°, b14 92°, n20D 1.4630, d2020 0.9560, surface tension σ20 34.34 ergs/cm.2 To a solution of 6.5 g. LiAlH4 in 600 ml. absolute Et2O at 0°, a solution of 25 g. IV in 200 ml. absolute Et2O was added dropwise during 2 hrs., and the mixture left overnight at room temperature and then refluxed 1.5 hrs. After the usual treatment, 89% I was obtained, b4 52°, n20D 1.4739, d2020 0.9096, σ20 32.67 ergs/cm.2 [I.PtCl6 m. 212° (decomposition); I.(AuCl4)2 m. 177° (decomposition); picrate m. 234° (decomposition)]. A solution of 30.2 g. Et nicotinate (b3 77-80°, n16D 1.504, d1616 1.1136, σ20 37.23 ergs/cm.2) in 600 ml. absolute EtOH was added to 62 g. Na, the reaction completed by short refluxing, and the solution decomposed by addition of 150 ml. H2O, concentrated in vacuo, and extracted with AcOEt. After fractionation, 57% II was obtained, b3 103-4°, n20D 1.4971, d2020 1.0283, σ20 44.39 ergs/cm.2

Dokl., Rossiisk. Sel’skokhoz. Akad. 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 C3H6O2, Formula: C7H16N2.

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