Thionyl Chloride → 2-(4-Chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 488752Notes

Reaction equation

HRID 488752 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH2:28]O)[CH:3]=1.S(Cl)([Cl:32])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH:11]2[CH3:25])=[O:9])=[C:4]([CH2:28][Cl:32])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 545634622-[4-Chloro-2-(hydroxymethyl)phenoxy]-1-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl}ethan-1-one

Product 1

HCID 219733932-(4-Chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(4-chloro-2-hydroxymethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.55 g, 1.3 mmol) in methylene chloride (6 ml) was added thionyl chloride (0.26 ml, 3.58 mmol). The reaction was heated to reflux for 2 hours. After cooling the reaction was quenched by the addition of water. The organic layer was washed with saturated sodium bicarbonate followed by saturated aqueous sodium chloride. The organic layer was then concentrated to afford the title compound as a yellow oil (0.52 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling the reaction
  4. customwas quenched by the addition of water
  5. washThe organic layer was washed with saturated sodium bicarbonate
  6. concentrationThe organic layer was then concentrated

Sources & evidence

ORD record
ord-0ca99f9caa814e71a4a88acfae270b6a
Source dataset
uspto-grants-2005_12
Patent number
US06974817B2

Reaction notes

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