Acetone → n-(4-Methoxybenzyl)propan-2-amine

A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield).

1. stirringthe resulting mixture was stirred at room temperature for 17 hours
2. customThe reaction mixture was quenched with 1 N NaOH (50 mL)
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with dichloromethane (2×20 mL)
5. washThe combined extracts were washed with water (20 mL), brine (20 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered through Celite
8. concentrationconcentrated under reduced pressure
9. customThe residue was chromatographed
10. washeluting with 10% MeOH in dichloromethane with 1% triethylamine

ORD record

ord-f034f2c108064e789ffabbeaf39cc6a5

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07521447B2