4-Chloropyridine hydrochloride → 4-Acetylamino-1-(4-pyridyl)piperidine

HRID 266750

Reaktionsgleichung

Reaktionsgleichung von HRID 266750
Cl.[C:2]([NH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])[CH3:3].Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CC(C)CCO>[C:2]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 114011054-Acetamidopiperidine dihydrochloride

Produkt 1

HCID 189184354-Acetylamino-1-(4-pyridyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31260Isoamyl AlcoholLösungsmittel

Versuchsvorschrift

A mixture of the product from step (ii) (1.79 g), 4-chloropyridine hydrochloride (1.50 g), sodium hydrogen carbonate (2.86 g) in 3-methyl 1-butanol (25 ml) was heated at reflux temperature for 16 hours. The cooled mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by flash chromatography on silica, eluting with methanol/dichloromethane (1:2 v/v) gave 4-acetylamino-1-(4-pyridyl)piperidine as a foam, 0.69 g: NMR(d6DMSO) δ 8.10(2H,d), 7.80(1H,bd), 6.80(2H,dd), 3.82(3H,m), 2.93(2H,dt), 1.78(3H,s), 1.77(2H,m), 1.33(2H,dq); m/e 220 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica
  6. washeluting with methanol/dichloromethane (1:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-7f5ef143010841d98ce0205fea76396f
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652242

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