Chloroacetyl chloride → 2-Chloro-1-{(2R)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl}ethan-1-one

HRID 11625Notes

Reaction equation

HRID 11625 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][C@H:9]([CH3:13])[CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>ClCCl>[Cl:23][CH2:24][C:25]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:8][C@H:9]1[CH3:13])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11600914(r)-1-(4-Fluorobenzyl)-3-methylpiperazine

Product 1

HCID 600606302-Chloro-1-{(2R)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl}ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (3R)-1-(4-fluoro-benzyl)-3-methyl-piperazine (3 g, 14.4 mmol) in dichloromethane (40 mL) was added triethylamine (2.0 mL, 14.4 mmol). The reaction was cooled to 0° C. and chloroacetyl chloride was added (1.1 mL, 14.4 mmol). The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction is diluted with dichloromethane and washed with 10% citric acid. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (3.9 g).

Workup

  1. temperatureto warm to ambient temperature
  2. washwashed with 10% citric acid
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03d958e6728f4420bdfbc1d54303f87c
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

Loading…