Acetic Acid → HCID 67705415, compound

HRID 1939979Notes

Reaction equation

HRID 1939979 reaction equation
[CH3:1]N(CN(C)C)C.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]3([CH2:28][C:27](=[O:29])[C:26]4[CH:30]=[C:31]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:32]=[CH:33][C:25]=4[O:24]3)[CH2:20][CH2:19]2)=[CH:12][CH:11]=1)#[N:9].C(O)(=O)C.C(=O)([O-])O.[Na+]>C1COCC1.O>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]3([C:28](=[CH2:1])[C:27](=[O:29])[C:26]4[CH:30]=[C:31]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])[CH:32]=[CH:33][C:25]=4[O:24]3)[CH2:20][CH2:19]2)=[CH:12][CH:11]=1)#[N:9]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 5829N,N,N',N'-Tetramethylmethanediamine2×HCID 516892Sodium BicarbonateHCID 10478362HCID 10478362, compound

Product 1

HCID 67705415HCID 67705415, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N,N,N',N'-Tetramethyldiaminomethane (1.36 ml, 1.02 g, 10 mmol) was added to a solution of 1'-[2-(4-cyanophenyl)ethyl]-3,4-dihydro-6-methanesulfonamidospiro(2H-1-benzopyran-2,4'-piperidine)-4-one (2.20 g, 5 mmol) and acetic acid (1.14 ml, 1.20 g, 20 mmol) in THF (40 ml) and the mixture was heated under reflux for 24 h. Further N,N,N',N'-tetramethyldiaminomethane (1.36 ml, 1.02 g, 10 mmol) and acetic acid (1.14 ml, 1.20 g, 20 mmol) were added and the mixture was heated under reflux for 6 h, cooled and poured into saturated aqueous sodium hydrogen carbonate (150 ml), diluted with water (50 ml) and extracted with methylene chloride (3×150 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. Toluene (600 ml) was added and the volume was reduced by distillation to 300 ml. Further toluene (300 ml) was added and the volume was reduced by distillation to 300 ml. The mixture was allowed to cool with stirring to room temperature then refrigerated overnight. The solid was collected and dried in vacuo to give the ketone as a yellow solid (1.98 g, 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 6 h
  5. temperaturecooled
  6. extractionextracted with methylene chloride (3×150 ml)
  7. dry with materialThe combined organic fractions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. additionToluene (600 ml) was added
  10. distillationthe volume was reduced by distillation to 300 ml
  11. additionFurther toluene (300 ml) was added
  12. distillationthe volume was reduced by distillation to 300 ml
  13. temperatureto cool
  14. customThe solid was collected
  15. customdried in vacuo

Sources & evidence

ORD record
ord-1c07f55fabdb44e3b91dc261fe581845
Source dataset
uspto-grants-1997_12
Patent number
US05698566

Reaction notes

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