1'-{3-[(2-Methylpropyl)oxy]-4-nitrophenyl}-1,4'-bipiperidine → 4-(1,4'-Bipiperidin-1'-yl)-2-[(2-methylpropyl)oxy]aniline

HRID 419342Notes

Reaction equation

HRID 419342 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O>[Ni].CCOC(C)=O>[N:20]1([CH:17]2[CH2:18][CH2:19][N:14]([C:7]3[CH:8]=[CH:9][C:10]([NH2:11])=[C:5]([O:4][CH2:3][CH:2]([CH3:26])[CH3:1])[CH:6]=3)[CH2:15][CH2:16]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 1

HCID 594526721'-{3-[(2-Methylpropyl)oxy]-4-nitrophenyl}-1,4'-bipiperidine

Product 1

HCID 594527114-(1,4'-Bipiperidin-1'-yl)-2-[(2-methylpropyl)oxy]anilineYield 39%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1′-{3-[(2-methylpropyl)oxy]-4-nitrophenyl}-1,4′-bipiperidine (4.00 g, 11.1 mmol) and Raney nickel (0.500 g) in EtOAc was stirred under H2 (1 atm.) for 1 h. The mixture was filtered through a pad of Celite®, concentrated and recrystallized from EtOAc/hexanes to provide the title compound (1.40 g, 4.20 mmol, 39%). MS (M+H) 332.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationconcentrated
  3. customrecrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-9f5e510ac22847a2b96f16bba9cb76c6
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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