1-(3-Chlorophenyl)piperazine → 6-{1-Oxo-2-[4-(3-chlorophenyl)-1-piperazinyl]-ethyl}-3,4-dihydrocarbostyril

HRID 1462531Notes

Reaction equation

[O:1]=[C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:3]Br.[Cl:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1>O1CCOCC1>[O:1]=[C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:3][N:26]1[CH2:25][CH2:24][N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 50 °C

Procedure

3.0 6-(1-oxo-2-bromoethyl)-3,4-dihydrocarbostyril and 5.5 g of 4-(3-chlorophenyl)piperazine were dispersed in 50 ml of dioxane and the dispersion was stirred at 50° C. for 5 hours. Then the reaction mixture was cooled and the insoluble matters formed in the reaction mixture were removed and the dioxane mother liquor was concentrated under a reduced pressure to dryness. 80 Milliliter of ether was added to the dried matter to effect the crystallization. Crude crystals thus obtained were recrystallized from dioxane-water to obtain 3.1 g of 6-{1-oxo-2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl}-3,4-dihydrocarbostyril in light yellow needle-like crystals.

Workup

temperatureThen the reaction mixture was cooled
customthe insoluble matters formed in the reaction mixture
customwere removed
concentrationthe dioxane mother liquor was concentrated under a reduced pressure to dryness
addition80 Milliliter of ether was added to the dried matter
customthe crystallization
customCrude crystals thus obtained
customwere recrystallized from dioxane-water

Sources & evidence

ORD record: ord-802ac941cff8416ba24890d0858d119b
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04460593

Reaction notes

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