Chloroacetyl chloride → 2-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 11631Notes

Reaction equation

HRID 11631 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][C@H:11]([CH3:13])[NH:10][CH2:9][C@H:8]2[CH3:14])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[Cl:24][CH2:25][C:26]([N:10]1[CH2:9][C@H:8]([CH3:14])[N:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:12][C@H:11]1[CH3:13])=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine

Product 1

HCID 113584612-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,5S)-1-(4-fluoro-benzyl)-2,5-dimethyl-piperazine (2.5 g, 11.2 mmol) in dry dichloromethane (11 mL) at 0° C. was added triethylamine (1.57 mL, 11.2 mmol) followed by chloroacetyl chloride (0.86 mL, 11.2 mmol). The resulting reaction mixture was stirred for 30 minutes. The reaction was then filtered through a pad of celite, washed with dichloromethane and the resulting filtrate was concentrated. Chromatography on silica gel gave the title compound (2.84 g).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction was then filtered through a pad of celite
  3. washwashed with dichloromethane
  4. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-560be2081f054067815e1cc2c2faf8c2
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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