1-(m-Tolyl)piperazine → 2-Methyl-3-[2-(4-m-tolyl-1-piperazinyl)ethyl]-7-chloro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1657407

Reaction equation

HRID 1657407 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:5]2[C:6](=[O:11])[C:7]=1[CH2:8][CH2:9]Cl.[C:17]1([CH3:29])[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:5]2[C:6](=[O:11])[C:7]=1[CH2:8][CH2:9][N:26]1[CH2:27][CH2:28][N:23]([C:19]2[CH:18]=[C:17]([CH3:29])[CH:22]=[CH:21][CH:20]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 831111-(m-Tolyl)piperazineHCID 124149402-methyl-3-(2-chloroethyl)-7-chloro-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 124148532-Methyl-3-[2-(4-m-tolyl-1-piperazinyl)ethyl]-7-chloro-4H-pyrido[1,2-a]pyrimidin-4-oneYield 39.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.3 g of 2-methyl-3-(2-chloroethyl)-7-chloro-4H-pyrido[1,2-a]pyrimidin-4-one, 2.1 g of 1-(m-tolyl)piperazine and 20 ml of toluene was refluxed for 30 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified by means of column chromatography using alumina and recrystallized from a mixture of ethanol and n-hexane to give 0.8 g of the desired compound as pale yellow scales, m.p. 119° - 120°C.

Workup

  1. temperaturewas refluxed for 30 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by means of column chromatography
  6. customrecrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-b2a14c58a0274586a01eddf82c134411
Source dataset
uspto-grants-1976_06
Patent number
US03960863

Linked notes

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