Ethanamine, 2,2,2-trifluoro- → HCID 22118605, compound

HRID 1274981Notes

Reaction equation

HRID 1274981 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[F:16])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[F:17][C:18]([F:22])([F:21])[CH2:19][NH2:20]>C1COCC1>[F:16][C:15]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:2][NH:20][CH2:19][C:18]([F:22])([F:21])[F:17]

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 21982898HCID 21982898, compound

Product 1

HCID 22118605HCID 22118605, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-bromomethyl-4-fluorobenzoate (14 g, 48 mmol) and 2,2,2-trifluoroethylamine (25 g, 250 mmol) in THF (300 mL) was stirred under argon at RT for 4 d, concentrated, and the residue partitioned between Et2O and 10% K2CO3. The organic phase was washed with 10% K2CO3 and brine, dried, and concentrated. The residue was purified by chromatography (silica gel, step gradient, 0-8% ethyl acetate/hexane) to give the title compound as a pale yellow oil (10.7, 72%): MS (ES) m/e 308.3[M+H]+.

Workup

  1. concentrationconcentrated
  2. customthe residue partitioned between Et2O and 10% K2CO3
  3. washThe organic phase was washed with 10% K2CO3 and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, step gradient, 0-8% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f1f8fb1e6094aa1a04669285c718c45
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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