Water → 6-[4-(3,4-Methylenedioxybenzoyl)-1-piperazinyl]carbostyril

HRID 1649253Notes

Reaction equation

HRID 1649253 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])[CH:12]=[CH:11]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH2:26]1[O:37][C:36]2[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]=2[O:27]1.O>CN(C=O)C>[CH2:26]1[O:37][C:36]2[CH:35]=[CH:34][C:30]([C:31]([N:5]3[CH2:6][CH2:7][N:2]([C:8]4[CH:9]=[C:10]5[C:15](=[CH:16][CH:17]=4)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]5)[CH2:3][CH2:4]3)=[O:32])=[CH:29][C:28]=2[O:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 132363676-(1-Piperazinyl)carbostyril hydrobromide

Product 1

HCID 132363586-[4-(3,4-Methylenedioxybenzoyl)-1-piperazinyl]carbostyrilYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-(1-Piperazinyl)carbostyril hydrobromide (2.0 g) was suspended in 20 ml of DMF. After adding 2.34 ml of triethylamine, a solution of 1.43 g of 3,4-methylenedioxybenzoyl chloride in 2 ml of DMF was added dropwise to the mixture. After completion of addition, the mixture was stirred at room temperature for 30 minutes and the reaction mixture was poured in a large amount of water. Crystals which formed were collected by filtration and dried. Then, the crystals were purified through silica gel column chromatography and recrystallized from chloroform-methanol to give 1.9 g of 6-[4-(3,4-methylenedioxybenzoyl)-1-piperazinyl]carbostyril, m.p. 266°-267° C. (decomp.), yellow powders.

Workup

  1. additionAfter completion of addition
  2. customCrystals which formed
  3. filtrationwere collected by filtration
  4. customdried
  5. customThen, the crystals were purified through silica gel column chromatography
  6. customrecrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-44530a4ccbf9445195e5871d672fd350
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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