Dichloromethane → 6-Chloro-2-(4-cyclopropanecarbonyl-1-piperazinyl)-pyrazine

HRID 261065Notes

Reaction equation

HRID 261065 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[N:5][CH:4]=1.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1.C(Cl)Cl>C(=O)([O-])[O-].[Na+].[Na+].O>[Cl:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][N:12]([C:18]([CH:15]3[CH2:17][CH2:16]3)=[O:19])[CH2:13][CH2:14]2)[CH:6]=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 77637Cyclopropanecarbonyl chlorideHCID 198421MK-212 hydrochloride

Product 1

HCID 203960016-Chloro-2-(4-cyclopropanecarbonyl-1-piperazinyl)-pyrazineYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred suspension of 4.70 g (20.0 mmol) of 6-chloro-2-(1-piperazinyl)-pyrazine hydrochloride in 75 ml saturated aqueous sodium carbonate cooled in an ice bath is added 3 ml (33 mmol) of cyclopropanecarboxylic acid chloride. The mixture is stirred 45 minutes at ice bath temperature and then treated with 5 ml methylene chloride and warmed to room temperature during 30 minutes. Additional acid chloride (3 ml, 33 mmol) is added and stirring is continued 30 minutes longer. The mixture is diluted with water and extracted with chloroform to give 5 g crude 6-chloro-2-(4-cyclopropanecarbonyl-1-piperazinyl)-pyrazine which crystallizes, mp 69°-71° C. (100%).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. waitis continued 30 minutes
  4. extractionextracted with chloroform

Sources & evidence

ORD record
ord-9c938ed1e24f40788e59c5891d546d37
Source dataset
uspto-grants-1979_08
Patent number
US04163849

Reaction notes

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