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

HRID 480179Notes

Reaction equation

HRID 480179 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 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R, 5S)-1-(4-fluoro-benzyl)-2,5-dimethyl-piperazine (2.5 g, 11.25 mmol) in dry dichloromethane (11 ml) at 0° C. was added triethylamine (1.57 ml, 11.2 mmol) followed by chloroacetyl chloride (0.858 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 to give a yellow oil Chromatography on silica get gave the title compound (2.84 g, 86% yield).

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
  5. customto give a yellow oil Chromatography on silica
  6. customget

Sources & evidence

ORD record
ord-46c22f7adc6e4dc785d5641d6e55f3a4
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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