Reaktion #60454

Reaktionsgleichung

sodium hydrogencarbonate

1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]piperazine

butyraldehyde

acetic acid

sodium triacetoxyborohydride

→

title compound

Ausbeute 64.2%

1-[4-Bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

Ausbeute 64.2%

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe separated organic layer was washed with water and brine in that order
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   FiltrationThe desiccant was filtered off
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To a mixture of the crude product of 1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]piperazine produced in Example (57a) (1.21 g), butyraldehyde (0.35 mL, 3.98 mmol), acetic acid (0.1 mL, 3.32 mmol) and tetrahydrofuran (8 mL) was added sodium triacetoxyborohydride (1.1 g, 4.98 mmol), followed by stirring for 2 hours and 10 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with water and brine in that order and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 901 mg of the title compound as a yellow oil.

Quelle