Water → 5-[4-(4-Methoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649211Notes

Reaction equation

HRID 1649211 reaction equation
Br.[N:2]1([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][C:12](=[O:18])[NH:13]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.O>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:9]=3[CH2:10][CH2:11][C:12](=[O:18])[NH:13]4)[CH2:3][CH2:4]2)=[O:33])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 204805915-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide

Product 1

HCID 132363425-[4-(4-Methoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (2.6 g) and 2.34 ml of triethylamine were dissolved in 40 ml of DMF. The mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.5 g of 4-methoxybenzoyl 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 hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 1.1 g of 5-[4-(4-methoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 219°-220° C., colorless needles.

Workup

  1. additionAfter completion of addition the reaction mixture
  2. stirringwas stirred for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off
  7. customresidual crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-b96a25f375e547de96f3ce2f53ef1fdd
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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