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N-{4-(methoxymethyl)-1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-N-phenylpropanamide → N-{1-[2-(4-aminophenyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide

HRID 1973845
Notes
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Reaction equation

HRID 1973845 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22](=[O:25])[CH2:23][CH3:24])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[H][H]>[Ni].CO>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:7]2[CH2:6][CH2:5][C:4]([N:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:22](=[O:25])[CH2:23][CH3:24])([CH2:3][O:2][CH3:1])[CH2:9][CH2:8]2)=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 12782363N-{4-(methoxymethyl)-1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-N-phenylpropanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 12782364N-{1-[2-(4-aminophenyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 14.8 parts of N-{4-(methoxymethyl)-1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-N-phenylpropanamide and 200 parts of methanol is hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The oily 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 oily residue is triturated in petroleumether. The product is filtered off and crystallized from a small amount of 2,2'-oxybispropane. It is filtered off and dried, yielding 8.23 parts of N-{1-[2-(4-aminophenyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide; mp. 106.2° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe oily 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. customThe oily residue is triturated in petroleumether
  8. filtrationThe product is filtered off
  9. customcrystallized from a small amount of 2,2'-oxybispropane
  10. filtrationIt is filtered off
  11. customdried

Sources & evidence

ORD record
ord-c64c4d3f2a3a4834a89b698fba5a97f3
Source dataset
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03998834

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes