Ammonium formate → 1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-pyridylmethyl)piperidine

HRID 1078628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078628
C(O[CH:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]23[CH2:33][CH:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=42)[C:25]2[C:20]3=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:14][CH2:13]1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)(=O)C.C([O-])=O.[NH4+]>[Pd].CO>[CH:21]1[C:20]2[C:19]3([CH2:18][N:15]4[CH2:14][CH2:13][CH:12]([CH2:5][C:6]5[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=5)[CH2:17][CH2:16]4)[CH2:33][CH:26]([C:27]4[C:32]3=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25]=2[CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formate2×HCID 231850921-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)4-piperidyl]-1-(3-pyridyl)methanol acetate

Produkt 1

HCID 196986881-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-pyridylmethyl)piperidineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-[1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidyl]-1-(3-pyridyl)methanol acetate, prepared as in Example 53, (175 mg, 0.40 mmol), ammonium formate (175 mg, 2.78 mmol), and 10% palladium on carbon (175 mg) were heated to reflux in methanol (6 mL) under nitrogen (g) for 8 h. Additional ammonium formate (175 mg, 2.78 mmol) was added and heating was continued for an additional 8 h. The suspension was filtered through celite and the solids were washed thoroughly with methanol and ethyl acetate. Concentration of the filtrate left an off white foam. Flash chromatography on silica using 3% methanol/dichloromethane gave the title compound as a colorless glass (100 mg, 0.26 mmol, 66%). This was dissolved in methanolic hydrogen chloride and concentrated from methanol (3×100 mL) to give the hydrochloride salt, mp 183°-185° C.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureheating
  3. filtrationThe suspension was filtered through celite
  4. washthe solids were washed thoroughly with methanol and ethyl acetate
  5. waitConcentration of the filtrate left an off white foam

Quellen und Nachweise

ORD-Eintrag
ord-a8ce0b34d35e4cdea0c62e779dedca41
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550136

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