2-(2,2,2-Trifluoroethoxy)-5-chlorobenzylamine hydrochloride → (2-(2,2,2-Trifluoroethoxy)phenyl)methanamine

HRID 1935444Notes

Reaction equation

HRID 1935444 reaction equation
Cl.[F:2][C:3]([F:16])([F:15])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:11](Cl)=[CH:10][C:7]=1[CH2:8][NH2:9]>C(O)C.[OH-].[OH-].[Pd+2]>[F:2][C:3]([F:15])([F:16])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][NH2:9]

Participants

4

Reactant 1

HCID 224645182-(2,2,2-Trifluoroethoxy)-5-chlorobenzylamine hydrochloride

Product 1

HCID 16772829(2-(2,2,2-Trifluoroethoxy)phenyl)methanamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(2,2,2-trifluoroethoxy)-5-chlorobenzylamine hydrochloride (650 mg) in ethanol (200 mL) containing 20% Pd(OH)2/C (1 g) was hydrogenated at 50 psi for 4 h. The catalyst was removed via filtration through Celite and the filtrate then evaporated to dryness to give the title compound as a white powder: 1H NMR (CD3OD) δ7.47 (m, 2H), 7.19 (m, 2H), 4.69 (q, J=8.4 Hz, 2H), 4.16 (s, 2H).

Workup

  1. customThe catalyst was removed via filtration through Celite
  2. customthe filtrate then evaporated to dryness

Sources & evidence

ORD record
ord-442888d82f8f4260a3044ebeba3c36ad
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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