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

HRID 1649210

Reaction equation

HRID 1649210 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:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1>CN(C=O)C.O.C(N(CC)CC)C>[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[C:10]4[C:15](=[CH:16][CH:17]=3)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]4)[CH2:3][CH2:4]2)=[O:47])=[CH:44][CH:43]=1

Participants

8

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

Product 1

HCID 132363156-[4-(4-Chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 16.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

6-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (3.5 g) was suspended in 40 ml of DMF. After adding 960 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 2.34 ml of triethylamine and the mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.5 g of 4-chlorobenzoyl chloride. After completion of addition the reaction mixture was stirred for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with saturated sodium hydrogen carbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol to give 0.7 g of 6-[4-(4-chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 233°-235° C., pale yellow needles.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. additionAfter completion of addition the reaction mixture
  3. stirringwas stirred for 30 minutes
  4. extractionextracted with chloroform
  5. washThe extract was washed with saturated sodium hydrogen carbonate 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-13d839316e2447508061ceae898791bd
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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