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

HRID 325080Notes

Reaction equation

HRID 325080 reaction equation
C(O[CH:4]=[N:5][C:6]1[S:17][C:9]2[CH2:10][N:11]([C:14](=[O:16])[CH3:15])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:18]([O:20]CC)=O)C.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])[CH2:28][CH2:27]1>C(O)C>[C:14]([N:11]1[CH2:12][CH2:13][C:8]2[C:7]3[C:18](=[O:20])[N:23]([CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][N:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[O:38][CH3:39])[CH2:30][CH2:31]4)[CH:4]=[N:5][C:6]=3[S:17][C:9]=2[CH2:10]1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazineHCID 541290012-Ethoxymethyleneamino-3-carboethoxy-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 98046243,4,5,6,7,8-Hexahydro-7-acetyl-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-oneYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.8 g (23.4 mmol) of 2-ethoxymethyleneamino-3-carboethoxy-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine in 50 ml of ethanol were mixed with 5.5 g (23.4 mmol) of 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine and refluxed for 2 h. The mixture was then concentrated in a rotary evaporator, and the residue was taken up in 30 ml of ethyl acetate, heated to boiling and left to cool with stirring. The solid which crystallized out was filtered off with suction after cooling in an ice bath and was washed with ethyl acetate. 8.7 g (80%) of product with melting point 170-172° C. were isolated.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe mixture was then concentrated in a rotary evaporator
  3. temperatureheated
  4. waitleft
  5. temperatureto cool
  6. customThe solid which crystallized out
  7. filtrationwas filtered off with suction
  8. temperatureafter cooling in an ice bath
  9. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-e06a8e4f27e14036a3f2cdafcfb2a921
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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