Dichloromethane → HCID 13646255, compound

HRID 1381191Notes

Reaction equation

HRID 1381191 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]([NH:9][C:10](=[O:18])[CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:35](Cl)=[O:36]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10](=[O:18])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[C:32]([O:31][CH3:30])[CH:33]=3)[CH2:14][CH2:13]2)=[CH:19][CH:20]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 11430Potassium CarbonateHCID 77070Veratroyl chlorideHCID 5302523HCID 5302523, compound

Product 1

HCID 13646255HCID 13646255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 Grams of p-methoxycarbonyl-α-(1-piperazinyl)acetanilide and 1.7 g of potassium carbonate were dissolved in 50 ml of DMF, then a methylene chloride solution containing 2.7 g of 3,4-dimethoxybenzoyl chloride was added dropwise thereto under ice-cooled condition with stirring. The reaction was continued at the same temperature for 2 hours, then to the reaction mixture was added 100 ml of methylene chloride, and the methylene chloride layer was washed with water, 5%-sodium bicarbonate aqueous solution, next with potassium carbonate aqueous solution, and was dried. Methylene chloride was removed by distillation, the residue obtained was purified by a silica gel column chromatography to obtain 3.3 g of p-methoxycarbonyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of oily substance.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooled condition
  3. washthe methylene chloride layer was washed with water, 5%-sodium bicarbonate aqueous solution, next with potassium carbonate aqueous solution
  4. customwas dried
  5. customMethylene chloride was removed by distillation
  6. customthe residue obtained
  7. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2ca709a9915943d482c27c1057a2456e
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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