Ethyl Acetate → HCID 23045007, compound

HRID 2108098Notes

Reaction equation

HRID 2108098 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(OCC)(=[O:24])C.C(=O)([O-])[O-].[K+].[K+].Cl.[C:35]([Cl:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1>O>[ClH:43].[ClH:1].[C:35]([N:12]1[CH2:13][CH2:14][N:9]([C:8](=[O:24])[C:7]2[CH:6]=[C:5]([O:4][CH3:3])[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][CH2:11]1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)2×HCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 23045007HCID 23045007, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1 g), ethyl acetate (50 ml), water (50 ml) and potassium carbonate (3 g) is added, with stirring at room temperature, nicotinoyl chloride hydrochloride (1 g). After stirring for 30 minutes, further nicotinoyl chloride hydrochloride (1 g) is added to the mixture, followed by stirring for another one hour. The ethyl acetate layer is separated, washed with an aqueous solution of sodium bicarbonate and water, successively, and dried, then the solvent is distilled off under reduced pressure. The residue is dissolved in a mixture of ethanol and ethyl acetate. To the mixture is added a 1N hydrogen chloride - ethyl acetate solution (10 ml). The mixture is diluted with ethyl ether, then precipitating powder is collected by filtration to yield 1-(nicotinoyl)-4-(3,4,5-trimethoxybenzoyl)piperazine dihydrochloride (0.8 g) as colorless powder.

Workup

  1. additionis added
  2. stirringAfter stirring for 30 minutes
  3. stirringby stirring for another one hour
  4. customThe ethyl acetate layer is separated
  5. washwashed with an aqueous solution of sodium bicarbonate and water
  6. customsuccessively, and dried
  7. distillationthe solvent is distilled off under reduced pressure
  8. dissolutionThe residue is dissolved in a mixture of ethanol and ethyl acetate
  9. additionTo the mixture is added a 1N hydrogen chloride - ethyl acetate solution (10 ml)
  10. additionThe mixture is diluted with ethyl ether
  11. customprecipitating powder
  12. filtrationis collected by filtration

Sources & evidence

ORD record
ord-4e3b492c89d44765aa339c690a642bc0
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

Loading…