Reaction #1605751

Reaction equation

2-methylheptan-4-one

ammonium acetate

sodium cyanoborohydride

→

2-methylheptan-4-amine

Yield 77.2%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with water and basified with 15% NaOH aqueous
3. 3
   Extractionextracted with ether
4. 4
   WashThe extract was washed with brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

To a solution of 2-methylheptan-4-one (4.24 g, 33.07 mmol), in methanol (60 mL), were added ammonium acetate (25.50 g, 330.71 mmol) and sodium cyanoborohydride (2.08 g, 33.07 mmol). The reaction mixture was stirred at room temperature for about 24 hours. The solvent was removed under reduced pressure and the residue was diluted with water and basified with 15% NaOH aqueous and extracted with ether. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 3.3 g of 2-methylheptan-4-amine (77%). MS (M+H, 130).

Source