Benzoyl chloride → HCID 23045025, compound

HRID 2108094Notes

Reaction equation

HRID 2108094 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[C:26]([Cl:34])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.C(OCC)(=O)C>[ClH:34].[C:26]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:8][CH2:9]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 1040951-[(3,4,5-Trimethoxyphenyl)methyl]piperazine

Product 1

HCID 23045025HCID 23045025, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine (0.5 g), potassium carbonate (3 g), ethyl acetate (30 ml) and water (20 ml) is added dropwise benzoyl chloride (1 ml) at room temperature with stirring. The mixture is stirred for one hour. Ethyl acetate (100 ml) and water (100 ml) are added to the mixture, followed by extraction. The ethyl acetate layer is separated, washed with water, dried, and concentrated under reduced pressure. The residue is dissolved in ethyl ether (200 ml). To the mixture is added hydrogen chloride - ethyl acetate (1N) (4 ml). Resultant precipitates are recrystallized from ethanol - ethyl ether to afford 1-benzoyl-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.5 g) as colorless powdery crystals, m.p. 220°-225° C. (decomp.).

Workup

  1. stirringThe mixture is stirred for one hour
  2. extractionfollowed by extraction
  3. customThe ethyl acetate layer is separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in ethyl ether (200 ml)
  8. additionTo the mixture is added hydrogen chloride - ethyl acetate (1N) (4 ml)
  9. customResultant precipitates
  10. customare recrystallized from ethanol - ethyl ether

Sources & evidence

ORD record
ord-2ffc75d483fe43838ab34b897af0e7d3
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

Loading…