Methanol → HCID 12298041, compound

HRID 1448317Notes

Reaction equation

HRID 1448317 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]=[C:15]([N:18]([C:25]1([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][CH3:17].[H][H].[CH3:37][OH:38]>[Pd]>[C:31]([OH:33])(=[O:32])[C:37]([OH:13])=[O:38].[O:14]=[C:15]([N:18]([C:25]1([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][N:28]([CH:10]2[CH2:11][CH2:12][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 786054-PhenylcyclohexanoneHCID 2724431Methyl 4-[phenyl(propanoyl)amino]piperidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12298041HCID 12298041, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
-20 °C

Procedure

A mixture of 4.3 parts of 4-phenyl-1-cyclohexanone, 4.3 parts of methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate and 80 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off. The filtrate is evaporated. The oily residue is purified by column-chromatography over silicagel using a mixture of trichloromethane and 7% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is converted into the ethanedioate salt in 2-propanol. After cooling to -20° C., the salt is filtered off and dried, yielding methyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-(4-phenylcyclohexyl)-4-piperidinecarboxylate ethanedioate; mp. 149.2° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customThe filtrate is evaporated
  3. customThe oily residue is purified by column-chromatography over silicagel
  4. additiona mixture of trichloromethane and 7% of methanol as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. filtrationthe salt is filtered off
  8. customdried

Sources & evidence

ORD record
ord-358434f9bd9543e28e8f77aecb47b92a
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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