4-Fluoroaniline → N-(4-Fluorophenyl)-4-piperidinamine

HRID 584613Notes

Reaction equation

HRID 584613 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[F: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>[F: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 97314-FluoroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5360545Sodium

Product 1

HCID 4778193N-(4-Fluorophenyl)-4-piperidinamine

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-fluoro-phenylamine (1.0 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 1.1 g, 63%

Sources & evidence

ORD record
ord-6573d05998ee48a99432f93fe135a8b7
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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