HCID 12298160, Verbindung → 4-Piperidinecarboxylic acid, 4-[(4-fluorophenyl)amino]-, methyl ester

HRID 1973807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973807
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22]([O:24][CH3:25])=[O:23])[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22]([O:24][CH3:25])=[O:23])[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 12298160HCID 12298160, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 122981784-Piperidinecarboxylic acid, 4-[(4-fluorophenyl)amino]-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 53 parts of methyl 4-[(4-fluorophenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylate and 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of palladium-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 15% of methanol, previously saturated with gaseous ammonia, as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on scratching in hexane. The product is filtered off and dried, yielding methyl 4-[(4-fluorophenyl)amino]-4-piperidinecarboxylate; mp. 83.7° C.

Aufarbeitung

  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 15% of methanol
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. filtrationThe product is filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-58cb91c175e2425e847317b5fe557ca9
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998834

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