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

HRID 2401545Notes

Reaction equation

HRID 2401545 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-b070ec2ba8ab43938b47308c37e5301a
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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