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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1973845
[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
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Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887Methanol
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c64c4d3f2a3a4834a89b698fba5a97f3
Quelldatensatz
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03998834

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