Methanol → Methyl-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate

HRID 382808노트

반응식

HRID 382808 반응식
[Mg].[CH2:2]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH:12]2[CH2:13][N:14]([CH3:23])[CH2:15][CH2:16]/[C:17]/2=[CH:18]\[C:19]([O:21][CH3:22])=[O:20])=[CH:6][C:5]=1[O:24][CH3:25])[CH3:3].[CH3:26][OH:27]>>[C:19]([O:21][CH2:22][CH3:26])(=[O:20])[CH3:18].[CH3:9][OH:10].[NH4+:14].[OH-:27].[CH2:2]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C@H:12]2[C@@H:17]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][N:14]([CH3:23])[CH2:13]2)=[CH:6][C:5]=1[O:24][CH3:25])[CH3:3].[CH3:22][O:21][C:19](=[O:20])[CH2:18][CH:17]1[CH2:16][CH2:15][N:14]([CH3:23])[CH2:13][CH:12]1[C:7]1[CH:6]=[C:5]([O:24][CH3:25])[C:4]([CH2:2][CH3:3])=[C:9]([O:10][CH3:11])[CH:8]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 5462224MagnesiumHCID 86757543methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate

생성물 3

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 57101424Methyl-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate수율 66%HCID 69823475Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate수율 20%

실험 절차

g 1) 25.76 g (1060 mmol) of magnesium shavings were added to a solution of 35.33 g (106 mmol) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate in 850 ml of methanol and the mixture was stirred at room temperature for 2 hours. The solution was filtered over Dicalite and evaporated. The residue was partitioned between 300 ml of methylene chloride and 500 ml of saturated ammonium chloride solution. The aqueous phase was extracted three times with 250 ml of methylene chloride. The organic phase was dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, ethyl acetate/methanol/NH4OH 200:10:1) yielded 7.16 g (20%) of methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.23 ((silica gel, ethyl acetate/methanol/NH4OH 200:10:1) and 23.51 g (66%) of methyl-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.12 (silica gel, ethyl acetatelmethanol/NH4OH 200:10:1).

후처리

  1. filtrationThe solution was filtered over Dicalite
  2. customevaporated
  3. customThe residue was partitioned between 300 ml of methylene chloride and 500 ml of saturated ammonium chloride solution
  4. extractionThe aqueous phase was extracted three times with 250 ml of methylene chloride
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-96cc412a6164410091fccdf9ba4ed43a
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310208B1

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