1-[3-(4-Nitrophenoxy)propyl]piperidine → 4-[3-(1-Piperidinyl)propoxy]aniline

HRID 502743Notes

Reaction equation

HRID 502743 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[N:12]1([CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 20579281-[3-(4-Nitrophenoxy)propyl]piperidine

Product 1

HCID 219749324-[3-(1-Piperidinyl)propoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[3-(4-nitrophenoxy)propyl]piperidine (15.5 g, 58.6 mmol) and 10% Pd/C (12.5 g) in 150 mL of EtOH was placed under a balloon of H2. The mixture was stirred for 18 h. The catalyst was removed by suction filtration and the organics concentrated to give the title compound as a yellowish oil. MS (m/z)=235.2 (M+H+); Calc'd for C14H22N2O=234.34.

Workup

  1. customThe catalyst was removed by suction filtration
  2. concentrationthe organics concentrated

Sources & evidence

ORD record
ord-1aa0612449444d31a2b767a0769661ce
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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