Ethanol → HCID 67327913, compound

HRID 1853950

Reaction equation

HRID 1853950 reaction equation
CN([CH:4]=[C:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[CH3:21])[CH2:6]1)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1.[C:33]([O-:36])(=[O:35])C.[Na+].[CH2:38]([OH:40])[CH3:39]>O>[CH3:23][O:36][C:33](=[O:35])[C:16]1[CH:15]=[CH:14][C:13]([CH3:21])=[C:12]([N:7]2[CH2:6][CH2:5][C:10]3([O:11][CH2:39][CH2:38][O:40]3)[CH2:9][CH2:8]2)[CH:17]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]2[N:32]=[CH:4][C:5]3[CH2:6][N:7]([C:12]4[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=4[CH3:21])[CH2:8][CH2:9][C:10]=3[N:31]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 673288983-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)piperidin-4-oneHCID 178512500HCID 178512500, compound

Product 2

HCID 67327913HCID 67327913, compoundHCID 673546753-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-Dimethylaminomethylene-1-(2-methyl-5-nitro-phenyl)-piperidin-4-one (12.06 gm, 41.7 mmol)[as prepared in reference 1] in Ethanol (250 ml) were added N-(4-Chloro-phenyl)-guanidine (28.32 gm, 167 mmol) and sodium acetate (27.32 gm, 334 mmol) and solution was heated under reflux for 12 hours. After cooling to room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine, dried [sodium sulfate] and concentrated under vacuum. The crude product obtained was further purified by silica gel chromatography using 5-10% Methanol/Chloroform as eluent to give pure desired product [11] i.e., (4-Chloro-phenyl)-[6-(2-methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-amine as yellow solid. (Yield: 2.50 gm, 15.2%)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried [sodium sulfate]
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-47ade73e82444c86a09c1581f508b7cf
Source dataset
uspto-grants-2015_02
Patent number
US08962637B2

Linked notes

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