Hydrochloric Acid → 1-Phenylpropan-1-amine

The mixture of 1-(7,8-dihydro-naphthalen-1-yl)-ethanone (10) (172 mg, 1.0 mmol) and 3-(3-trifluoromethyl-phenyl)-propylamine (13) (204 mg, 1.0 mmol) in titanium (IV) isopropoxide (1 mL) was stirred at room temperature overnight. Methanol(5 mL) was added followed by addition of sodium borohydride (55 mg, 2.0 mmol). The reaction mixture was stirred at room temperature for 1 hour and evaporated to dryness. The crude product was purified by chromatography on silica gel, loaded with dichloromethane and eluted with 2% methanol in dichloromethane containing 0.5% ammonium hydroxide. The pure fractions were combined and evaporated to give a colorless oil. The product was converted to a hydrochloride salt by addition of 1 N HCl in ethyl ether. Evaporation gave compound (1) as an off-white solid (325 mg, 82.2%).

1. stirringThe reaction mixture was stirred at room temperature for 1 hour
2. customevaporated to dryness
3. customThe crude product was purified by chromatography on silica gel
4. washeluted with 2% methanol in dichloromethane containing 0.5% ammonium hydroxide
5. customevaporated
6. customto give a colorless oil
7. customEvaporation

ORD record

ord-5b464b77cffb46488b0b0d07513a59eb

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361789B1