Reaktion #336055

Reaktionsgleichung

piperdine

title compound

N-Benzyl-N-methyl-2-chloroethylamine Hydrochloride

NaHCO3

→

title compound

Ausbeute 58.5%

2-(N-Benzyl-N-methylamino)-1-(N-piperidinyl)ethane

Ausbeute 58.5%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter filtration
2. 2
   Einengenthe filtrate was concentrated to a yellow murky oil
3. 3
   workup.DISSOLUTIONThe oil was dissolved into a 1.0M KOH solution (10 mL)
4. 4
   Extraktionwas extracted with EtOAc (3×5 mL)
5. 5
   WaschenThe organic layer was washed with a 5% NaHCO3, solution (5 mL), H2O (5 mL), and brine (5 mL)
6. 6
   Trocknenwas dried over MgSO4
7. 7
   EinengenThe filtrate was concentrated
8. 8
   Sonstigepurified by medium pressure column chromatography on silica gel [eluting NH4OH-EtOH-CHCl3 (1:5:94)]

Vorschrift

A solution of piperdine (1.16 g, 13.6 mmol), the title compound of Step 10 (3.0 g, 13.6 mmol) and NaHCO3 (3.94 g, 46.9 mmol) in EtOH (24 mL) was refluxed overnight in a modification of the procedure of Bach, et al. [J. Am. Chem. Soc. 79, 2221-2225 (1957)]. After filtration, the filtrate was concentrated to a yellow murky oil. The oil was dissolved into a 1.0M KOH solution (10 mL) and was extracted with EtOAc (3×5 mL). The organic layer was washed with a 5% NaHCO3, solution (5 mL), H2O (5 mL), and brine (5 mL) and then was dried over MgSO4. The filtrate was concentrated and purified by medium pressure column chromatography on silica gel [eluting NH4OH-EtOH-CHCl3 (1:5:94)] to give 1.85 g (58% yield) of the title compound as an oil. The proton spectral data were consistent with the proposed structure.

Quelle