Sulfuric Acid → 10-Benzyl-3,10-diazabicyclo[4.3.1]decan-4-one

HRID 1912338

반응식

HRID 1912338 반응식
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH:9]1[CH2:10][C:11](=[O:17])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[N-:23]=[N+]=[N-].[Na+].C([O-])([O-])=O.[K+].[K+].[OH-].[K+]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH:9]1[CH2:10][NH:23][C:11](=[O:17])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 33557Sodium AzideHCID 4195319-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

생성물 1

HCID 4579274510-Benzyl-3,10-diazabicyclo[4.3.1]decan-4-one수율 95%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 9-benzyl-9-azabicyclo[3.3.1]nonan-3-one (0.5 g) in chloroform (4.4 ml), cooled down to −5° C., 1 ml of conc. H2SO4 is dropwise added while maintaining the temperature below 15° C. Then NaN3 (0.28 g) is slowly added, at small portions so to avoid temperatures in the reaction mixture higher than 35° C. The mixture is then heated at reflux for 2 hours. The reaction mixture is poured into a vessel containing about 200 ml of ice. Solid K2CO3 is added up to a strongly alkaline pH. An emulsion is formed, that is added of 25 ml of a 60% KOH aqueous solution. Stirring is effected for 10 minutes. At the end the formed inorganic salts are filtered and the reaction mixture extracted with chloroform. The organic phase is dehydrated with sodium sulphate and the solvent evaporated. 0.50 g of 10-benzyl-3,10-diazabicyclo[4.3.1]decan-4-one (1py1) are obtained as a light solid.

후처리

  1. temperaturewhile maintaining the temperature below 15° C
  2. customhigher than 35° C
  3. temperatureThe mixture is then heated
  4. temperatureat reflux for 2 hours
  5. additionThe reaction mixture is poured into a vessel
  6. customAn emulsion is formed
  7. filtrationAt the end the formed inorganic salts are filtered
  8. extractionthe reaction mixture extracted with chloroform
  9. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-5b1c90349f3a475eab5c9027473a2366
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609659B2

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