Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate → tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

HRID 1779077Notes

Reaction equation

HRID 1779077 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH2:10]2)=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%; 510 mg) was added to a solution of tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate (A111) (2.21 g, 6.86 mmol) in methanol (30 mL) and the resulting mixture was stirred under a hydrogen atmosphere overnight. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure to afford the title compound A112 (1.13 g, 56%); 1H NMR (300 MHz, CDCl3); δ 6.68 (d, J=8.8 Hz, 2H), 6.52 (d, J=8.7 Hz, 2H), 4.17 (m, 1H), 3.63 (m, 4H), 3.20 (m, 2H), 1.78 (m, 2H), 1.61 (m, 2H), 1.40 (s, 9H). LCMS-B: rt 5.05 min; m/z 293.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-1989944c8bbd45fd9a60009b24c7bc5c
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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