1-(2-Methyl-6-nitrophenyl)piperidine → 3-Methyl-2-(1-piperidinyl)aniline

HRID 32906Notes

Reaction equation

HRID 32906 reaction equation
[CH3:1][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]>[CH3:1][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 127982131-(2-Methyl-6-nitrophenyl)piperidine

Product 1

HCID 693077873-Methyl-2-(1-piperidinyl)anilineYield 91%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using a procedure similar to Example 3, step (c), 1-(2-methyl-6-nitro-phenyl)-piperidine (74 mg, 0.38 mmol, as prepared in the previous step) was stirred with 5% Pd—C (50 mg) under H2 to afford 66 mg (91%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C12H18N2, 191.1 (M+H), found 191.1.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-94a17360d02d4a83b6358d68d467f9a1
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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