1-Phenylpiperazine → 2-(4'-Phenyl-piperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine

HRID 258691Notes

Reaction equation

HRID 258691 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:14]1[N:15]=[CH:16][C:17]2[C:23](=[O:24])[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][N:20]([CH2:30][CH3:31])[C:18]=2[N:19]=1.Cl.C1(N2CCNCC2)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:14]3[N:15]=[CH:16][C:17]4[C:23](=[O:24])[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][N:20]([CH2:30][CH3:31])[C:18]=4[N:19]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 70961-PhenylpiperazineHCID 751641-Phenylpiperazinium chlorideHCID 122668052-Chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydropyrido(2,3-d)pyrimidine

Product 1

HCID 122668072-(4'-Phenyl-piperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidineYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.2 g of (0.02 mol) of N-phenyl-piperazine in 30 cm3 of toluene is added to 2.8 g (0.01 mol) of 2-chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine dissolved in 30 cm3 of toluene. Reaction takes place practically instantaneously with evolution of heat and the mixture sets solid due to formation of phenylpiperazine hydrochloride. The mixture is diluted with 100 cm3 of ethyl acetate, the solution is filtered, washed with water and dried (MgSO4) and the solvent is evaporated. The residue is recrystallised from 110 cm3 of isopropanol and yields 3.38 g (84%) of 2-(4'-phenyl-piperazino)-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine; melting point 186° C.

Workup

  1. customReaction
  2. temperatureof heat
  3. filtrationthe solution is filtered
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe residue is recrystallised from 110 cm3 of isopropanol

Sources & evidence

ORD record
ord-d273dd4b042743c0b3e7da8da7e0ded9
Source dataset
uspto-grants-1977_07
Patent number
US04034094

Reaction notes

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