Hexahydro-1,4-diazepine → N,N'-bis[[5-(3,4,5-Trimethoxyphenyl)-thiophen-2-yl]methyl]homopiperazine Dimaleate

HRID 993038Notes

Reaction equation

HRID 993038 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[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50]>CO>[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]\[C:49]([OH:51])=[O:50].[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]\[C:49]([OH:51])=[O:50].[CH3:19][O:18][C:10]1[CH:9]=[C:8]([C:5]2[S:4][C:3]([CH2:2][N:39]3[CH2:45][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 68163Hexahydro-1,4-diazepineHCID 444972Fumaric AcidHCID 184084922-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiopheneHCID 184085302-Chloromethyl-5-(3,4,5-trimethoxyphenyl)thiophene

Product 1

HCID 86758583N,N'-bis[[5-(3,4,5-Trimethoxyphenyl)-thiophen-2-yl]methyl]homopiperazine Dimaleate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiophene (230 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 homopiperazine (41 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 fumaric 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-e4ca4b5ccfb248a393a17706a874de75
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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