Methanol → HCID 86734311, compound

HRID 1973818Notes

Reaction equation

HRID 1973818 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[O:11]=[C:12]([N:15]([C:22]1([C:28]([O:30][CH3:31])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][CH3:14].[H][H].[CH3:34][OH:35]>[Pd]>[CH3:1][CH:2]([O-:10])[CH3:3].[C:28]([O-:30])(=[O:29])[C:34]([O-:10])=[O:35].[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:25]1[CH2:26][CH2:27][C:22]([N:15]([C:12](=[O:11])[CH2:13][CH3:14])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:28]([O:30][CH3:31])=[O:29])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 887MethanolHCID 119832-IndanoneHCID 2724431Methyl 4-[phenyl(propanoyl)amino]piperidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86734311HCID 86734311, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 2 parts of 1,3-dihydro-2H-inden-2-one, 4.4 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 and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is dissolved in 2,2'-oxybispropane. The solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is converted into the ethanedioate salt in 4-methyl-2-pentanone. The salt is filtered off and crystallized from 2-propanol, yielding methyl 1-(2,3-dihydro-1H-inden-2-yl)-4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate ethanedioate 2-propanolate; mp. 206° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and 5% of methanol as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. dissolutionThe residue is dissolved in 2,2'-oxybispropane
  8. filtrationThe latter is filtered off
  9. customthe filtrate is evaporated
  10. filtrationThe salt is filtered off
  11. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-73f1840c0dea4a55a7a4aac9f060d40d
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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