1-Piperazinecarboxaldehyde → HCID 13089623, compound

HRID 258690Notes

Reaction equation

HRID 258690 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 one hour. After cooling, the solution is washed with water and dried and the solvent is evaporated. The oily residue crystallises on being taken up in 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 one 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-f2f61e84d7d04c68bb859e5460c4a010
Source dataset
uspto-grants-1977_07
Patent number
US04034094

Reaction notes

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