Dimethyl Sulfoxide → 5-[4-(4-Aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrate

HRID 1649226Notes

Reaction equation

[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[NH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][Cl:34])=[CH:31][CH:30]=1>O>[OH2:17].[ClH:34].[ClH:34].[NH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[CH2:9][CH2:10][C:11](=[O:17])[NH:12]4)[CH2:2][CH2:3]2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1.2 g of 5-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium carbonate and 20 ml of dimethyl sulfoxide was added 650 mg of 4-aminobenzyl chloride and the mixture was stirred at 80° C. for 2.5 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Chloroform was distilled off and the residue was purified through silica gel column chromatography. After conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether to give 0.4 g of 5-[4-(4-aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrate, m.p. 224°-227° C. (decomp.), yellow granules.

Workup

extractionextracted with chloroform
washAfter washing with water
dry with materialthe extract was dried over anhydrous sodium sulfate
distillationChloroform was distilled off
customthe residue was purified through silica gel column chromatography
customAfter conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether

Sources & evidence

ORD record: ord-d29db4f53c1a4a4f82307da6de3e000a
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415572

Reaction notes

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