Dimethylformamide → HCID 21472303, compound

HRID 1649228Notes

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+].CN(C=O)C.[CH3:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][Cl:34])=[CH:31][CH:30]=1>O>[ClH:34].[ClH:34].[CH3:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH: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:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1.2 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium bicarbonate and 20 ml of DMF was added 646 mg of 4-methylbenzyl 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-water to give 0.17 g of 6-[4-(4-methylbenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride, m.p. 272°-273° C. (decomp.), colorless powders.

Workup

extractionextracted with chloroform
washAfter washing with water the extract
dry with materialwas 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-water

Sources & evidence

ORD record: ord-a00be88f49d7444d91c2c9988a98cd03
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415572

Reaction notes

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