Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

HRID 633410Notes

Reaction equation

HRID 633410 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)=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[C:6]([C:24]([F:27])([F:25])[F:26])[CH:5]=1

Participants

4

Reactant 1

HCID 22181018Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 22180984Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate (0.75 g, 1.0 eq, 1.9 mmol) and Pd—C (10%, 0.3 g) in EtOH (50 mL) was hydrogenated at 30 psi for 2 hours. The mixture was filtered through celite and the filter cake washed with EtOH (2×10 mL). The filtrate was concentrated under vacuum to give the desired product in 90% yield. This product was taken to next step with out further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake washed with EtOH (2×10 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-71e8a325e5d541708ec9c989a4d2f78c
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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