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

HRID 852453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852453
[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-3b4a9062767d496b8a2e96c5abe8c3ff
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253157B2

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