4-Piperidinecarboxylic acid → 1-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine

HRID 223557

반응식

HRID 223557 반응식
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=O)[CH2:3][CH2:2]1.S(Cl)(Cl)=[O:11].C[O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:29](Cl)[CH3:30]>>[C:29]([N:1]1[CH2:2][CH2:3][CH:4]([C:5](=[O:7])[C:17]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=2[OH:15])[CH2:8][CH2:9]1)(=[O:11])[CH3:30]

참가 물질

6

반응물 5

HCID 37734-Piperidinecarboxylic acidHCID 63651,1-DichloroethaneHCID 90161,4-DimethoxybenzeneHCID 24386Thionyl Chloride3회HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 130763841-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine

실험 절차

To a stirred mixture of 60.0 g of isonipecotic acid and 290 ml of 1,2-dichloromethane, at 40°, was added dropwise, 27 ml of thionyl chloride, dissolved in 27 ml of dichloroethane. After 50% of the thionyl chloride had been added, the temperature was raised to 65°. After complete addition of the thionyl chloride, the reaction mixture was stirred at 65° for 1 hr. The reaction mixture was cooled to 20° and 48.6 g of 1,4-dimethoxybenzene was added, followed by the slow addition of 93.6 g of aluminum chloride. The solution was heated under reflux for 4 hrs, the dichloroethane was decanted from the insoluble complex, and concentrated hydrochloric acid was added. The acid hydrolysate was added to the dichloroethane solution and the mixture was extracted three times with chloroform. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give an oil. The oil was scratched with a glass rod until crystallization was effected. The solid was collected to yield 87.0 g of product. Recrystallization twice from isopropyl ether gave an analytically pure product, mp, 93°-94°.

후처리

  1. additionat 40°, was added dropwise
  2. temperaturethe temperature was raised to 65°
  3. temperatureThe reaction mixture was cooled to 20°
  4. temperatureThe solution was heated
  5. temperatureunder reflux for 4 hrs
  6. customthe dichloroethane was decanted from the insoluble complex, and concentrated hydrochloric acid
  7. additionwas added
  8. additionThe acid hydrolysate was added to the dichloroethane solution
  9. extractionthe mixture was extracted three times with chloroform
  10. extractionThe organic extract
  11. washwas washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was removed in vacuo
  14. customto give an oil
  15. customThe oil was scratched with a glass rod until crystallization
  16. customThe solid was collected

출처 및 근거

ORD 기록
ord-a008fed1622a424897178425804476a0
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04355037

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