Trimethylamine → HCID 13236331, compound

HRID 1649231Notes

Reaction equation

HRID 1649231 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN(C)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[CH2:9][CH2:10][C:11](=[O:17])[NH:12]4)[CH2:2][CH2:3]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 73974-Toluenesulfonyl chlorideHCID 11630008HCID 11630008, compound

Product 1

HCID 13236331HCID 13236331, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-(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 1.07 g of p-toluenesulfonyl 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 saturated saline solution 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 DMF to give 800 mg of 5-[4-(p-toluenesulfonyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 302°-304° C., colorless powders.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at the same temperature as above for 30 minutes
  3. additionThe reaction mixture was poured into a large amount of saturated saline solution
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationChloroform was distilled off
  8. customresidual crystals were recrystallized from DMF

Sources & evidence

ORD record
ord-d2cd4af6f04c4e5b9d95b8d061ca5ff9
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

Loading…