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

HRID 1649209

Reaction equation

HRID 1649209 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0adb51efa4434b288b741add56e93f20
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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