Water → (S)-3-(1-(4-bromophenyl)ethylamino)-1-(2-fluorophenyl)propan-1-one

HRID 2037522Notes

Reaction equation

HRID 2037522 reaction equation
CN(C)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:6].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=1.O>CCO>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([NH:24][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:6])[CH3:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 581091723-(Dimethylamino)-1-(2-fluorophenyl)propan-1-one

Product 1

HCID 59635692(S)-3-(1-(4-bromophenyl)ethylamino)-1-(2-fluorophenyl)propan-1-oneYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylamino-1-(2-fluoro-phenyl)-propan-1-one (17 g, 0.087 mol) and (S)-1-(4-bromophenyl)ethanamine (17 g, 0.087 mol) in EtOH (50 mL)/H2O (50 mL) was refluxed at 80° C. over night. The solvent was removed under vacuum. The residue was purified by column chromatography to afford (S)-3-(1-(4-bromophenyl)ethylamino)-1-(2-fluorophenyl)propan-1-one (1 g, 3%).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-95a3d59f718d4beda48091a9ffa1e10f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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