Reacción #52489

Ecuación de reacción

1-(4-bromophenyl)-cyclopropylamine

Intermediate 116

1-(4-bromophenyl)-cyclopropylamine

THF

propionaldehyde

NaCNBH3

→

title compound

[1-(4-Bromophenyl)-cyclopropyl]-dipropylamine

Disolventes

CH3CN HOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with H2O
2. 2
   Extracciónextracted with EtOAc
3. 3
   LavadoThe combined extracts were washed with H2O and saturated aqueous NaCl
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of 1-(4-bromophenyl)-cyclopropylamine (Intermediate 116) in CH3CN/HOAc (5 mL, 9:1, v/v) and THF 3 mL at 0° C. was added propionaldehyde (277.0 mg, 4.95 mmols) and NaCNBH3 (153.0 mg, 2.47 mmols). The reaction was warmed to room temperature and after 5 hours quenched with H2O. The pH of the solution was adjusted to 8-9 using aqueous NaOH and extracted with EtOAc. The combined extracts were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound, 190.0 mg (56%), was isolated by column chromatography (2-5% EtOAc—hexanes).

Fuente