Hydrochloric Acid → Hydrocodone

HRID 2375508노트

반응식

HRID 2375508 반응식
CC(C)([O-])C.[K+].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:21][N:22]1[C@@H:38]2[CH2:39][C:27]3[CH:28]=[CH:29][C:30]([O:41][CH3:42])=[C:31]4[O:32][C@H:33]5[C@@H:34]([OH:40])[CH2:35][CH2:36][C@@H:37]2[C@:25]5([C:26]=34)[CH2:24][CH2:23]1.Cl>C1C=CC=CC=1>[CH3:21][N:22]1[C@@H:38]2[CH2:39][C:27]3[CH:28]=[CH:29][C:30]([O:41][CH3:42])=[C:31]4[O:32][C@H:33]5[C:34]([CH2:35][CH2:36][C@@H:37]2[C@:25]5([C:26]=34)[CH2:24][CH2:23]1)=[O:40]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 5284543DihydrocodeineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 5284569Hydrocodone수율 62.2%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a mixture of 1.25 g (11.1 mmol) of potassium-t-butoxide in 50 mL of benzene were added 6.78 g (37 mmol) of benzophenone and 1.12 g (3.7 mmol) of dihydrocodeine, which was allowed to reflux for 2 hours. The reaction mixture turned yellow. The reaction mixture was allowed to cool to room temperature, and 50 mL of 2N HCl was added. The resulting reaction mixture was allowed to stir for 10 minutes. The organic layer was separated and extracted with 3×40 mL of 2N HCl. The organic layer was discarded, and the aqueous layer was again extracted with 3×20 mL of dichloromethane. The aqueous layer was basified with aqueous potassium hydroxide solution to pH 12 and extracted with 5×60 mL of dichloromethane. The organic layers were combined and dried over MgSO4 and filtered. The filtrate was concentrated to give 691 mg (2.3 mmol, 55%) of 3 as a yellow solid.

후처리

  1. temperatureto reflux for 2 hours
  2. customThe resulting reaction mixture
  3. customThe organic layer was separated
  4. extractionextracted with 3×40 mL of 2N HCl
  5. extractionthe aqueous layer was again extracted with 3×20 mL of dichloromethane
  6. extractionextracted with 5×60 mL of dichloromethane
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-400c1a96f9994157867ab13e3153ce1d
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465797B2

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