4-Chloroaniline → N-(4-chlorophenyl)piperidin-4-amine

HRID 584612Notes

Reaction equation

HRID 584612 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[Na]>ClCCl.C(O)(=O)C.FC(F)(F)C(O)=O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 78124-ChloroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5360545Sodium

Product 1

HCID 7183033N-(4-chlorophenyl)piperidin-4-amine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

Was synthesised in the same way as (A) from 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (3.59 g, 18.0 mmol), 4-chloro-phenylamine (1.15 g, 9.0 mmol) and sodium triacetoxyborhydride (5.34 g, 25.2 mmol) in dichloromethane (40 ml) and acetic acid (3.1 ml). The deprotection was run in dichloromethane (37 ml) and trifluoro acetic acid (18 ml). Yield 1.5 g, 79%

Sources & evidence

ORD record
ord-20419aa56fb04dbc94c63111deb83e03
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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