tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate synthesis

5synthesis methods

Product Name:tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate
CAS Number:872850-30-1
Molecular formula:C13H22N2O2
Molecular Weight:238.33

tert-butyl 4-((ethoxycarbonyl)(cyano)methyl)-4-methylpiperidine-1-carboxylate

872850-29-8
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tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate

872850-30-1
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Yield:872850-30-1 86%

Reaction Conditions:

with water;lithium chloride in dimethyl sulfoxide at 160; for 2.5 h;

Steps:

H.3

Step 3: Preparation of tert-buty 4-(cyanomethyl)-4-methylpiperidine-l-carboxylate; CNTo a solution of tert-butyl 4-(l-cyano-2-ethoxy-2-oxoethyl)-4-methylpiperidine-l-carboxylate (13. 3g, 42.8mmol) in DMSO (120ml) and water (1.5ml) was added lithiumchloride (2.54g) and the resulting mixture was heated to 160°C for 2.5 hours. The reactionwas cooled to room temperature and water (200ml) was added. The mixture was extractedwith diethyl ether (800ml), washed with brine and dried. Evaporation under reduced pressureyielded a tan solid (8.77g, 86%); NMR (CDC1₃): 1.1 (s, 3H), 1.4 (m, 13H), 2.2 (s, 2H), 3.1-3.2(m, 2H), 3.5 (m, 2H).

References:

WO2006/1752,2006,A1 Location in patent:Page/Page column 72