Ethyl Acetate → 2-(1-Benzylpiperidin-4-ylamino)-5-methylpyridine

HRID 2223873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223873
Br[C:2]1[CH:7]=[C:6](C)[CH:5]=[CH:4][N:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[C:23](OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:10]([NH:9][C:2]2[CH:7]=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=2)[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 4158521-Benzyl-4-piperidylamineHCID 516892Sodium BicarbonateHCID 27340872-Bromo-4-methylpyridine

Produkt 1

HCID 230211122-(1-Benzylpiperidin-4-ylamino)-5-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To 2-bromo-4-methylpyridine (15.5 g) was added 4-amino-1-benzylpiperidine (68.5 g). The resulting solution was stirred at 180° C. for 9 hours and then at 150° C. for 6 hours. Ethyl acetate and water were then added to the solution followed by addition of saturated aqueous sodium bicarbonate solution. After separating liquid layers, the organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)] to give the title compound (11.5 g).

Aufarbeitung

  1. waitat 150° C. for 6 hours
  2. customAfter separating liquid layers
  3. washthe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)]

Quellen und Nachweise

ORD-Eintrag
ord-d660c6c007a742718f1d7d9b80c272a8
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375115B2

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