HCID 53880935, compound → HCID 58723639, compound

HRID 1696459Notes

Reaction equation

HRID 1696459 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][CH2:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][CH2:8][NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 1

HCID 53880935HCID 53880935, compound

Product 1

HCID 58723639HCID 58723639, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(3-nitrophenethyl)-2,2,2-trifluoroacetamide (9.05 g, 34.5 mmol) in MeOH (125 ml) at RT was added 10% Pd/C (50% H2O wet) (3.67 g, 1.73 mmol). The resulting suspension was placed under H2 (3 atm) at RT overnight. The reaction was filtered through Celite® and the cake rinsed with MeOH. The filtrate was concentrated to provide N-(3-aminophenethyl)-2,2,2-trifluoroacetamide as an oil (7.83 g, 98% yield). 1H NMR (300 MHz, CDCl3): δ 7.16-7.12 (m, 1H), 6.62-6.58 (m, 2H), 6.54-6.53 (m, 1H), 6.34 (brs, 1H), 3.61 (q, J=6.40 Hz, 2H), 2.80 (t, J=6.40 Hz, 2H), 2.68 (brs, 2H); MS (ESI) m/z: 233.3 (M+H+).

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. washthe cake rinsed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-847d4b17db6149b6a798aa2c37fca611
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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