1-[(4-Methoxyphenoxy)carbonylmethyl]-4-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride → KB-5492 free base

HRID 2291551Notes

Reaction equation

HRID 2291551 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]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)[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[CH2:14][CH2:15][N:16]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)[CH2:17][CH2:18]2)=[O:11])=[CH:32][CH:33]=1

Participants

3

Reactant 1

HCID 141001161-[(4-Methoxyphenoxy)carbonylmethyl]-4-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride

Product 1

HCID 131083KB-5492 free baseYield 76%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

The 1-[(4-methoxyphenoxy)carbonylmethyl]-4-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (8.0 g) obtained above is added to a 5% aqueous potassium carbonate solution (100 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-(3,4,5-trimethoxybenzyl)piperazine (5.2 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-3fefa20d7a8d4f0bbf393a8f8e39eaa1
Source dataset
uspto-grants-1989_01
Patent number
US04797400

Reaction notes

Loading…