Benzoyl chloride, 3-chloro- → 6-[4-(3-Chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649209

반응식

HRID 1649209 반응식
Br.[N:2]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].N1(C2C=C3C(=CC=2)NC(=O)CC3)CCNCC1.[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45](Cl)=[O:46]>CN(C=O)C.O.C(N(CC)CC)C>[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:3][CH2:4]1)=[O:46]

참가 물질

8

반응물 4

HCID 69252Benzoyl chloride, 3-chloro-HCID 516892Sodium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

생성물 1

HCID 132363246-[4-(3-Chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril수율 35.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매

실험 절차

6-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (1 g) was suspended in 15 ml of DMF. After adding 296 mg of sodium hydrogencarbonate, the suspension was stirred at room temperature for 30 minutes to convert the starting compound to 6-(1-piperazinyl)-3,4-dihydrocarbostyril. Then, to the mixture was added 0.62 ml of triethylamine and the mixture was stirred at room temperature while slowly adding dropwise 5 ml of DMF solution containing 532 mg of m-chlorobenzoyl chloride. After completion of addition the reaction mixture was stirred for at room temperature 1 hour. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol to give 0.4 g of 6-[4-(3-chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 197°-197.5° C., colorless scales.

후처리

  1. stirringthe mixture was stirred at room temperature
  2. additionAfter completion of addition the reaction mixture
  3. stirringwas stirred for at room temperature 1 hour
  4. extractionextracted with chloroform
  5. washThe extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationChloroform was distilled off
  8. customresidual crystals were recrystallized from methanol

출처 및 근거

ORD 기록
ord-0adb51efa4434b288b741add56e93f20
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415572

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