Trimethylamine → HCID 13236321, compound

HRID 1649232Notes

Reaction equation

HRID 1649232 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.CN(C=O)C.CN(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>O>[CH3:27][S:28]([N:4]1[CH2:5][CH2:6][N: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)[CH2:2][CH2:3]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 6228Dimethylformamide2×HCID 31297Methanesulfonyl chlorideHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13236321HCID 13236321, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1-Piperazinyl)-3,4-dihydrocarbostyril (1.0 g) was added to a mixture of 10 ml of DMF and 0.85 ml of trimethylamine and the mixture was stirred at room temperature while slowly adding dropwise 5 ml of DMF solution containing 440 mg of methanesulfonyl chloride. After completion of addition, the reaction mixture was stirred at the same temperature as above for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol to give 0.17 g of 6-(4-methanesulfonyl-1-piperazinyl)-3,4-dihydrocarbostyril, m.p. 241.5°-243° C., colorless granules.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at the same temperature as above for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed 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-4df8f73852494e5c8192f691b0d2ef1a
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

Loading…