Acetyl chloride → 1-[2-(S)-Benzyl-4-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazin-1-yl]-ethanone

HRID 737134Notes

Reaction equation

HRID 737134 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](Cl)(=[O:33])[CH3:32].C(N(CC)C(C)C)(C)C>ClCCl>[CH2:1]([C@H:8]1[CH2:9][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:28])[F:29])=[CH:17][CH:16]=2)[CH2:11][CH2:12][N:13]1[C:31](=[O:33])[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 578494973-(S)-benzyl-1-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine

Product 1

HCID 578496121-[2-(S)-Benzyl-4-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

45 mg of 3-(S)-benzyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine was dissolved in dichloromethane, 1.1 equiv. of acetylchloride and 1.5 equiv. of N,N-diisopropylethylamine were added. The reaction was stirred at room temperature under nitrogen overnight. The reaction was diluted with DCM, washed with saturated aqueous sodium bicarbonate solution, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to afford 51 mg of the title compound as free base. Yield 84%, Treatment with 1 equiv. of 1M HCl in dioxane gave the HCl salt. ES MS(+) m/z 453

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a2b303bea19426ea440ac85fa3b27bf
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

Loading…