Hydrochloric Acid → 4-(4-Chlorophenyl)piperidine-4-carbonitrile

HRID 1036336Notes

Reaction equation

HRID 1036336 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([C:14]#[N:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Product 1

HCID 229935654-(4-Chlorophenyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (1.000 g, 3.12 mmol) in methanol (5 ml) at rt was added 4M HCl in dioxane (15 ml). After stirring for 20 h the solution was concentrated to give the deprotected amine as the hydrochloride salt (0.785 g, 98%). LC-MS (LCT2) m/z 221 [M+H+], Rt 12.84 min.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-92475b50d90d43769e7affea90ce9da0
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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