Triethylamine → o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

HRID 1381190Notes

Reaction equation

HRID 1381190 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[NH:7][C:8](=[O:16])[CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:4].C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[NH:7][C:8](=[O:16])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:30]([O:29][CH3:28])[CH:31]=2)[CH2:12][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 13117362o-Methoxycarbonyl-alpha-(1-piperazinyl)acetanilide

Product 1

HCID 13117363o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.5 Grams of o-methoxycarbonyl-α-(1-piperazinyl)acetanilide and 2.4 g of triethylamine were dissolved in 50 ml of methylene chloride, then a methylene chloride solution containing 5.4 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 1 hour, then the reaction mixture 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 crystallized by adding ethyl acetate, the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 7.5 g of o-methoxycarbonyl-α-[4-(3,4-dimethoxy-benzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169° C.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooled condition
  3. washthe reaction mixture 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 crystallized
  8. additionby adding ethyl acetate
  9. customthe crystals formed
  10. filtrationwere collected by filtration
  11. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-7fd697e16f894d51828b886afb75e08b
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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