Dimethylformamide → HCID 13243490, compound

HRID 1649224Notes

Reaction equation

HRID 1649224 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1>O>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]4)[CH2:2][CH2:3]2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13243490HCID 13243490, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.0 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.11 g of potassium carbonate and 20 ml of DMF was added 780 mg of 4-chlorobenzyl chloride and the mixture was stirred at 70°-80° C. for 4 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. Chloroform was distilled off and the residue was purified through silica gel column chromatography. Recrystallization from chloroform-methanol gave 500 mg of 6-[4-(4-chlorobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 190°-191.5° C., colorless needles.

Workup

  1. extractionextracted with chloroform
  2. distillationChloroform was distilled off
  3. customthe residue was purified through silica gel column chromatography
  4. customRecrystallization from chloroform-methanol

Sources & evidence

ORD record
ord-6b0d1980fe394422b1d0cb78e75b9f25
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

Loading…