1-Piperazinecarboxaldehyde → HCID 13089623, compound

HRID 1605255Notes

Reaction equation

HRID 1605255 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=2[N:7]=1.[CH:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21]>C(Cl)(Cl)Cl>[CH:20]([N:22]1[CH2:27][CH2:26][N:25]([C:2]2[N:3]=[CH:4][C:5]3[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=3[N:7]=2)[CH2:24][CH2:23]1)=[O:21]

Participants

4

Reactant 2

HCID 821911-PiperazinecarboxaldehydeHCID 122668052-Chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydropyrido(2,3-d)pyrimidine

Product 1

HCID 13089623HCID 13089623, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 8.4 g of 2-chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine, 6.9 g of formylpiperazine and 160 cm3 of chloroform is heated under reflux for 1 hour. After cooling, the solution is washed with water and dried and the solvent is evaporated. The oily residue crystallises on being taken up to 100 cm3 of isopropyl ether. The solid is filtered off and recrystallised from 50 cm3 of ethanol and yields 8.9 g (82%) of 2-(4'-Formylpiperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine which melts in two stages; melting point 195°C, solidification, followed by m.p. 204°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. washthe solution is washed with water
  5. customdried
  6. customthe solvent is evaporated
  7. customThe oily residue crystallises
  8. filtrationThe solid is filtered off
  9. customrecrystallised from 50 cm3 of ethanol

Sources & evidence

ORD record
ord-a3aca5c0aa4140d2954c081215f3df80
Source dataset
uspto-grants-1976_04
Patent number
US03950338

Reaction notes

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