Hydrochloric Acid → 4-Methylpiperidine-4-carbonitrile hydrochloride

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]#[N:16])([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C.CO.[ClH:19]>>[ClH:19].[CH3:14][C:11]1([C:15]#[N:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 46835621tert-Butyl 4-cyano-4-methylpiperidine-1-carboxylate

Product 1

HCID 575166104-Methylpiperidine-4-carbonitrile hydrochloride

Procedure

In a round-bottomed flask, 4-cyano-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (0.35 g, 1.56 mmol) was dissolved in hydrogen chloride, 1.0 M solution in methanol (9.0 mL, 9.00 mmol). The reaction mixture was stirred at room temperature overnight then concentrated to give 0.27 g of 4-methyl-piperidine-4-carbonitrile hydrochloride as an off-white foam which was used without further purification.