Reacción #60451

Ecuación de reacción

sodium hydrogencarbonate

1-[2-(3,3,4,4-tetramethylcyclopentyl)phenyl]piperazine

propionaldehyde

sodium triacetoxyborohydride

acetic acid

propionaldehyde

sodium triacetoxyborohydride

→

1-propyl-4-[2-(3,3,4,4-tetramethylcyclopentyl)phenyl]piperazine

Rendimiento 5.2%

Disolventes

tetrahydrofuran

ethyl acetate

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 18 hours and 30 minutes at room temperature
3. 3
   ConcentraciónThe obtained organic layers were concentrated
4. 4
   OtroThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Procedimiento

To a solution of the 1-[2-(3,3,4,4-tetramethylcyclopentyl)phenyl]piperazine (20 mg, 0.0698 mmol) produced in Example (55b) in tetrahydrofuran (1 mL) were added propionaldehyde (0.0065 mL, 0.0908 mmol), sodium triacetoxyborohydride (19.2 mg, 0.0908 mmol) and acetic acid (0.0076 mL, 0.133 mmol), followed by stirring for 3 hours at room temperature. After further adding propionaldehyde (0.0065 mL, 0.0908 mmol), sodium triacetoxyborohydride (19.2 mg, 0.0908 mmol) and 1,2-dichloroethane (1 mL) to the reaction mixture, stirring was continued for 18 hours and 30 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed three times with ethyl acetate. The obtained organic layers were concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1.2 mg of 1-propyl-4-[2-(3,3,4,4-tetramethylcyclopentyl)phenyl]piperazine as a colorless oil.

Fuente