1-Piperazineacetic acid, 4-((2,3,4-trimethoxyphenyl)methyl)-, 4-methoxyphenyl ester, dihydrochloride → 1-[(4-Methoxyphenoxy)carbonylmethyl]-4-(2,3,4-trimethoxybenzyl)piperazine

HRID 2291549Notes

Reaction equation

HRID 2291549 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([O:9][C:10]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[C:21]=3[O:30][CH3:31])[CH2:15][CH2:14]2)=[O:11])=[CH:7][CH:6]=1>C(=O)([O-])[O-].[K+].[K+]>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[C:21]=3[O:30][CH3:31])[CH2:15][CH2:14]2)=[O:11])=[CH:32][CH:33]=1

Participants

3

Reactant 1

HCID 30872121-Piperazineacetic acid, 4-((2,3,4-trimethoxyphenyl)methyl)-, 4-methoxyphenyl ester, dihydrochloride

Product 1

HCID 30872131-[(4-Methoxyphenoxy)carbonylmethyl]-4-(2,3,4-trimethoxybenzyl)piperazineYield 47.6%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

The 1-[(4-methoxyphenoxy)carbonylmethyl]-4-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride (15 g) obtained above is added to a 5% aqueous potassium carbonate solution (70 ml), and the produced oily substance is extracted with chloroform (150 ml). The chloroform layer is dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is recrystallized from a mixture of ethyl acetate and n-hexane to give 1-[(4-methoxyphenoxy)carbonylmethyl]-4-(2,3,4-trimethoxybenzyl)piperazine (6.1 g).

Workup

  1. extractionthe produced oily substance is extracted with chloroform (150 ml)
  2. dry with materialThe chloroform layer is dried over anhydrous magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ace353689f8b452a8d0579964cb494eb
Source dataset
uspto-grants-1989_01
Patent number
US04797400

Reaction notes

Loading…