Dimethylformamide → HCID 13236320, compound

HRID 1649219Notes

Reaction equation

HRID 1649219 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C=O)C.[CH2:30]1[O:41][C:40]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][C:32]=2[O:31]1>O>[CH2:30]1[O:41][C:40]2[CH:39]=[CH:38][C:34]([C:35]([N:4]3[CH2:5][CH2:6][N:1]([C:7]4[CH:8]=[C:9]5[C:14](=[CH:15][CH:16]=4)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]5)[CH2:2][CH2:3]3)=[O:36])=[CH:33][C:32]=2[O:31]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13236320HCID 13236320, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 2.34 ml of triethylamine were added to 40 ml of DMF. The mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.7 g of 3,4-methylenedioxybenzoyl chloride. After completion of addition, the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with 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 1.6 g of 6-[4-(3,4-methylenedioxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 191°-192.5° C., colorless needles.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with 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

Sources & evidence

ORD record
ord-18f304466c9e4c1aa5c9da8651123a21
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

Loading…