Piperazine → N,N'-bis[[5-(3,4,5-Trimethoxyphenyl)-thiophen-2-yl]methyl]piperazine Dimaleate

HRID 993037Notes

Reaction equation

HRID 993037 reaction equation
O[CH2:2][C:3]1[S:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:6][CH:7]=1.Cl[CH2:21][C:22]1[S:23][C:24]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=2)=[CH:25][CH:26]=1.[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49]>CO>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]\[C:48]([OH:50])=[O:49].[CH3:19][O:18][C:10]1[CH:9]=[C:8]([C:5]2[S:4][C:3]([CH2:2][N:39]3[CH2:44][CH2:43][N:42]([CH2:21][C:22]4[S:23][C:24]([C:27]5[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=5)=[CH:25][CH:26]=4)[CH2:41][CH2:40]3)=[CH:7][CH:6]=2)[CH:13]=[C:12]([O:14][CH3:15])[C:11]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 444266Maleic AcidHCID 184084922-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiopheneHCID 184085302-Chloromethyl-5-(3,4,5-trimethoxyphenyl)thiophene

Product 1

HCID 86758582N,N'-bis[[5-(3,4,5-Trimethoxyphenyl)-thiophen-2-yl]methyl]piperazine Dimaleate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiophene (234 mg) was treated in the same manner in Preparation Example 4 to synthesize 2-chloromethyl-5-(3,4,5-trimethoxyphenyl)thiophene. Since this product was unstable, it was immediately reacted with piperazine (36 mg) in the same manner in Example 1 without isolating it to obtain a product as a free base. This product was dissolved in methanol, and maleic acid was added to the solution, thereby converting it into the title compound.

Workup

  1. customwithout isolating it
  2. customto obtain a product as a free base

Sources & evidence

ORD record
ord-591f3b5d6a5e4566a6c25b03327464b8
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

Loading…