Hydrochloric Acid → 6-{4-[4-(3-Chlorophenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril

HRID 1285448Notes

Reaction equation

O[CH:2]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH2:8][CH2:7]1.Cl.[OH-].[Na+].CCOCC>C(O)(=O)C>[Cl:18][C:14]1[CH:13]=[C:12]([N:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH:3]=[CH:2][C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)[CH2:11][CH2:10]2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.9 Grams of 6-{1-hydroxy-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril was dissolved in 50 ml of acetic acid and further 2 ml of concentrated hydrochloric acid was added to this solution. The solution was stirred at 80° C. for 30 minutes and the reaction mixture was concentrated under a reduced pressure to dryness to obtain a residue. To the residue were added 10N-NaOH and ether and stirred at a room temperature for 30 minutes. The crystals thus precipitated were collected by filtration and separated by a silica-gel chromatography. Recrystallized from ethanol-chloroform to obtain 6-{4-[4-(3-chlorophenyl)-1-piperazinyl]-1-butenyl}-3,4-dihydrocarbostyril in colorless prism-like crystals. Yield: 1.6 g. Melting point: 175°-176° C.

Workup

concentrationthe reaction mixture was concentrated under a reduced pressure to dryness
customto obtain a residue
stirringstirred at a room temperature for 30 minutes
customThe crystals thus precipitated
filtrationwere collected by filtration
customseparated by a silica-gel chromatography
customRecrystallized from ethanol-chloroform

Sources & evidence

ORD record: ord-b5ec8cdc16ab48c3b8761c781ff4d647
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567187

Reaction notes

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