Thiophene → (+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetate

HRID 490868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490868
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.S1C=CC=C1.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 8030ThiopheneHCID 22499408(+/-)-Methyl 1-(4-nitrophenyl)-alpha-phenyl-4-piperidineacetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22499374(+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetateAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate (14) (0.0022 mole) in methanol (100 ml) was hydrogenated at 50° C. with palladium-on-carbon (10%) (0.1 g) as a catalyst in the presence of a 4% thiophene solution (0.1 ml). After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in hexane. The precipitate was filtered off and dried, yielding 0.7 g of (±)-methyl 1-(4-aminophenyl)-α-phenyl-4-piperidineacetate (intermediate 15, melting point 125° C.).

Aufarbeitung

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in hexane
  3. filtrationThe precipitate was filtered off
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-05fe50ff46724dd5b6a0efca7ea5f535
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528154B2

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