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

HRID 382808Notes

Reaction equation

HRID 382808 reaction equation
[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

Participants

6

Reactant 3

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

Product 3

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-96cc412a6164410091fccdf9ba4ed43a
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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