Sodium Bicarbonate → KB-5492 free base

HRID 2291550Notes

Reaction equation

HRID 2291550 reaction equation
Cl.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.Cl[CH2:23][C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:25].C(=O)([O-])O.[Na+]>C(#N)C>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24]([CH2:23][N:12]2[CH2:13][CH2:14][N:9]([CH2:8][C:7]3[CH:6]=[C:5]([O:4][CH3:3])[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=3)[CH2:10][CH2:11]2)=[O:25])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5324604-Methoxyphenyl chloroacetateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 131083KB-5492 free base

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (prepared by the method disclosed in Belgian Pat. No. 560,330) (50 g), 4-methoxyphenyl chloroacetate (prepared by the method disclosed in U.S. Pat. No. 3,657,318) (33 g), sodium hydrogen carbonate (49 g) and acetonitrile (700 ml) is stirred at 60° C. for 3 hours. The reaction mixture is filtered, and the filtrate is concentrated under reduced pressure to give crude 1-[(4-methoxyphenoxy)carbonylmethyl]-4-(3,4,5-trimethoxybenzyl)piperazine (free base) (60 g) as an oily substance. This crude free base (60 g) is dissolved in a mixture of water (200 ml) and acetonitrile (50 ml) and thereto is added fumaric acid of about 2 moles (41 g) to 1 mole of the free base, and the mixture is heated. After the reaction mixture is allowed to cool at room temperature, the precipitated crystals are separated by filtration and recrystallized from a mixture of water and acetonitrile to give 1-[(4-methoxyphenoxy)carbonylmethyl]-4-(3,4,5-trimethoxybenzyl)piperazine difumarate monohydrate (73.5 g) as colorless crystals.

Workup

  1. customprepared by the method
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-144f365eac6449b9a22af2d25fd6e072
Source dataset
uspto-grants-1989_01
Patent number
US04797400

Reaction notes

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