Reaction #1833277

Reaction equation

(Trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropanamine

2-cyclohexylacetaldehyde

NaBH4

→

(Trans)-2-(4-(3-bromobenzyloxy) phenyl)-N-(2-cyclohexylethyl)cyclopropane amine

Yield 21.0%

Solvents

DCE

Conditions

Workup

1. 1
   OtherAfter completion, the reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in Methanol (15 mL)
3. 3
   workup.STIRRINGstirred for 3 h
4. 4
   Extractionextracted with EtOAc (2×50 mL)
5. 5
   WashThe combined organic layers were washed with brine (50 mL)
6. 6
   Dryingdried over anhydrous Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated
9. 9
   OtherThe crude residue was purified by flash column chromatography

Procedure

To a solution of (Trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropanamine (2 g, 6.2 mmol) and 2-cyclohexylacetaldehyde (790 mg, 6.2 mmol) in DCE (20 mL) sodium triacetoxy borohydrate (2.3 g, 2 equiv) was added slowly at 0° C. and stirred for 20 h. After completion, the reaction mixture was evaporated. The residue was dissolved in Methanol (15 mL) and NaBH4 (627 mg, 3 equiv) was added slowly at 0° C. to the reaction mixture and stirred for 3 h. After completion, the reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash column chromatography by using EtOAc: Pet ether to get (Trans)-2-(4-(3-bromobenzyloxy) phenyl)-N-(2-cyclohexylethyl)cyclopropane amine (500 mg, 21%) as a pale yellow liquid.

Source