1-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine → 3,4,5,6,7,8-Hexahydro-2,7-dimethyl-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)-ethyl]-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-one

HRID 325078Notes

Reaction equation

HRID 325078 reaction equation
[C:1]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([CH3:15])[CH2:10][C:9]=2[S:8][C:7]=1[N:16]=[C:17](OCC)[CH3:18])([O:3]CC)=O.[NH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[CH2:27][CH2:26]1>C(O)C>[CH3:18][C:17]1[N:22]([CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[CH2:29][CH2:30]2)[C:1](=[O:3])[C:6]2[C:14]3[CH2:13][CH2:12][N:11]([CH3:15])[CH2:10][C:9]=3[S:8][C:7]=2[N:16]=1

Participants

4

Reactant 2

HCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazineHCID 54227348Ethyl n-(3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno-[2,3-c]pyridin-2-yl)ethaneimidate

Product 1

HCID 224647283,4,5,6,7,8-Hexahydro-2,7-dimethyl-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)-ethyl]-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-oneYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.9 g (6.2 mmol) of ethyl N-(3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)ethanimidate in 30 ml of ethanol were mixed with 1.5 g (6.2 mmol) of 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine and refluxed for 7 h. The mixture was then concentrated in a rotary evaporator, and the residue was taken up in 20 ml of ethyl acetate. 2.1 g of crude product crystallized out overnight and were filtered off with suction and purified by column chromatography (silica gel, mobile phase methylene chloride/methanol 92/8). 0.8 g (29%) of product was isolated.

Workup

  1. temperaturerefluxed for 7 h
  2. concentrationThe mixture was then concentrated in a rotary evaporator
  3. custom2.1 g of crude product crystallized out overnight
  4. filtrationwere filtered off with suction
  5. custompurified by column chromatography (silica gel, mobile phase methylene chloride/methanol 92/8)

Sources & evidence

ORD record
ord-c0abd7aa2437416cab8deb18c88e5f6d
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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