Water → 3-[3-(Trifluoromethyl)phenyl]propan-1-amine

Temperature

0 °C

To an ice-bath cooled suspension of sodium hydride (1.32 g of a 60% dispersion in oil, 33 mmol) in anhydrous tetrahydrofuran (100 ml) under a nitrogen atmosphere was added dropwise a solution of diethyl cyanomethylphosphonate (5.34 ml, 33 mmol) in tetrahydrofuran (40 ml) and the resulting mixture stirred at 0° C. for 15 minutes. To this mixture was added a solution of 3-trifluoromethylbenzaldehyde (5.22 g, 30 mmol) in anhydrous tetrahydrofuran (40 ml) and the resulting mixture stirred at room temperature for 1.5 hours. Water (300 ml) was added and the mixture extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with water (2×200 ml), brine (150 ml) then dried (Na2SO4) and evaporated. The residue was taken up in a mixture of ethanol (100 ml) and ammonium hydroxide (25 ml) and hydrogenated according to the method of Description 2. Purification by column chromatography on silica eluting with 5% MeOH in dichloromethane+0.5% NH4OH gave the title compound (1.5 g, 25%) as a yellow oil.

1. temperatureTo an ice-bath cooled
2. stirringthe resulting mixture stirred at room temperature for 1.5 hours
3. extractionthe mixture extracted with ethyl acetate (3×150 ml)
4. washThe combined organic layers were washed with water (2×200 ml), brine (150 ml)
5. dry with materialthen dried (Na2SO4)
6. customevaporated
7. additionThe residue was taken up in a mixture of ethanol (100 ml) and ammonium hydroxide (25 ml)
8. customPurification by column chromatography on silica eluting with 5% MeOH in dichloromethane+0.5% NH4OH

ORD record

ord-e93d5e1630ba4fc58b32633118a9adac

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2