4,4-Difluoro-1-(2-nitrophenyl)piperidine → 2-(4,4-Difluoropiperidin-1-yl)aniline

HRID 32897Notes

Reaction equation

HRID 32897 reaction equation
[F:1][C:2]1([F:17])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:4][CH2:3]1>CO.[Pd]>[F:17][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 693093544,4-Difluoro-1-(2-nitrophenyl)piperidine

Product 1

HCID 693077102-(4,4-Difluoropiperidin-1-yl)anilineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Using a procedure similar to Example 3, step (c), 4,4-difluoro-1-(2-nitro-phenyl)-piperidine (128 mg, 0.520 mmol, as prepared in the previous step) was stirred with 80 mg 5% Pd—C in 4 mL of MeOH under H2 to afford 76 mg (69%) of the title compound as a dark oil, which was used immediately due to apparent instability. Mass spectrum (ESI, m/z): Calcd. for C11H14F2N2, 213.1 (M+H), found 213.1.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-93fb4fa7e03f4d25ba3f715eedd7afbb
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

Loading…