Reaction #52489

Reaction equation

1-(4-bromophenyl)-cyclopropylamine

Intermediate 116

1-(4-bromophenyl)-cyclopropylamine

THF

propionaldehyde

NaCNBH3

→

title compound

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

Solvents

CH3CN HOAc

Conditions

Workup

1. 1
   Otherquenched with H2O
2. 2
   Extractionextracted with EtOAc
3. 3
   WashThe combined extracts were washed with H2O and saturated aqueous NaCl
4. 4
   Dryingdried (MgSO4)
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

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).

Source