1-(2-Chloro-6-nitrophenyl)piperidine → 3-Chloro-2-piperidin-1-yl-phenylamine

HRID 32903Notes

Reaction equation

HRID 32903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>[Pd]>[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 47789671-(2-Chloro-6-nitrophenyl)piperidine

Product 1

HCID 9523943-Chloro-2-piperidin-1-yl-phenylamineYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using a procedure similar to Example 3, step (c), 1-(2-chloro-6-nitro-phenyl)-piperidine (79 mg, 0.32 mmol, as prepared in the previous step) was stirred with 44 mg of 5% Pd—C under H2 for 1 h 30 min to afford 54 mg (80%) of the title compound, contaminated with the des-chloro derivative, which was used immediately without further purification. Mass spectrum (ESI, m/z): Calcd. for C11H15ClN2, 211.0 (M+H), found 211.1.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-e22a07edd6ec4b7b933a3074f4d49e15
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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