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

HRID 496192Notes

Reaction equation

HRID 496192 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-bda73295b8ac4d90aaa250f609ca7ada
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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