Reacción #60445

Ecuación de reacción

cyclopropylacetaldehyde

1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

sodium triacetoxyborohydride

acetic acid

sodium hydrogencarbonate

→

1-(2-cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

Disolventes

ethyl acetate

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe organic layer was concentrated
2. 2
   Otrothe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Procedimiento

To a solution of cyclopropylacetaldehyde in 1,2-dichloroethane (0.29 M, 5 mL) were added 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (25 mg, 0.0832 mmol) produced in Example (8b), sodium triacetoxyborohydride (22.9 mg, 0.108 mmol) and acetic acid (0.009 mL, 0.158 mmol), followed by stirring for 20 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed twice with ethyl acetate. The organic layer was concentrated and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 20.9 mg of 1-(2-cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine as a colorless oil.

Fuente