Hydrochloric Acid → 4-[(4-Chlorophenyl)methyl]-4-piperidinemethanamine

HRID 1470266Notes

Reaction equation

HRID 1470266 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C:11]2([CH2:14][NH2:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 248292211,1-Dimethylethyl 4-[(4-chlorophenyl)methyl]-4-cyano-1-piperidinecarboxylate

Product 1

HCID 248288594-[(4-Chlorophenyl)methyl]-4-piperidinemethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-chlorobenzyl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (0.500 g, 1.493 mmol) in methanol (3 ml) was added 4M HCl in dioxane (10 ml). After stirring for 19 hours, the solution was concentrated to give the deprotected amine as the hydrochloride salt (0.405 g).

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-c2e335349198416391da5fd4a9cd890a
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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