Sodium Hydroxide → 2-(4-Benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 1252282Notes

Reaction equation

HRID 1252282 reaction equation
S(O)(O)(=O)=O.[C:6]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)(=[NH:8])[NH2:7].[OH-].[Na+].[CH2:24]([N:26]1[CH2:31][CH2:30][C:29](=O)[C:28](=[CH:33]OC)[C:27]1=[O:36])[CH3:25]>C(O)C>[CH2:15]([N:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:7]=[CH:33][C:28]3[C:27](=[O:36])[N:26]([CH2:24][CH3:25])[CH2:31][CH2:30][C:29]=3[N:8]=2)[CH2:10][CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 540921521-Ethyl-3-methoxymethylenepiperidine-2,4-dione

Product 1

HCID 137841212-(4-Benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.56 g of 1-amidino-4-benzylpiperazine sulfate was added to an ethanol solution containing 0.23 g of sodium hydroxide. To the resulting suspension was added 1.07 g of 1-ethyl-3-methoxymethylenepiperidine-2,4-dione, and they were refluxed for 2 hours. Ethanol was distilled off. Then, water was added and extraction by chloroform was conducted. The chloroform layer was dried and concentrated to obtain 1.4 g of 2-(4-benzylpiperazino)-6-ethyl-5-oxo-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine with an yield of 69%.

Workup

  1. temperaturewere refluxed for 2 hours
  2. distillationEthanol was distilled off
  3. additionThen, water was added
  4. extractionextraction by chloroform
  5. dry with materialThe chloroform layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f629056016ba4afcb8c7b4085a1f4a0f
Source dataset
uspto-grants-1988_05
Patent number
US04742165

Reaction notes

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