2-(4-TRIFLUOROMETHYL-PHENYL)-ETHYLAMINE

(4-Trifluoromethyl-phenyl)-acetonitrile (2g, 10.81mmol) in methanolic ammonia (50mL) was added to Raney nickel (400mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10percent methanol in CHC1Step 1: To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2 N NH3/MeOH (400 mL) was added Raney Ni (-4. 0 g). The reaction mixture was placed in a Parr Apparatus and hydrogentated under 50 lb pressure of H2 overnight. The solution was filtered through celite and concentrated IN VACUO to yield the desired amine (38 g, 95percent). ESI-MS calc. For CGHIOF3N : 189; Found: 190 (M+H)To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (~4. 0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9HlOF3N : 189; Found: 190 (M+H).INTERMEDIATE 13; To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (-4. 0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated iM vacuo to yield the desired amine (38 g, 95percent).To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+M).EXAMPLES INTERMEDIATE 1 Step A; To a solution of 4- trifluoromethyl phenylacetonitrile (40 g, 220 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni ((at)4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 1b pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+H).To a solution of 4- trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni ((at)4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+H).General procedure: Under nitrogen atmosphere, ethanol (30 mL), immediate III (3 mmol) and titanium (IV) isopropoxide (9 mmol) were added to a three-necked round bottom flask and stirred for 0.5 h, then the substituted ethylamine (3 mmol) was dropped into the solution and stirred for 3 h at room temperature. Subsequently, sodium borohydride (4.5 mmol) was added to the flask slowly, the reductive amination reaction was maintained for 3 h. According to the TLC monitoring results, the ammonia water (2 mol L-1, 10 mL) was poured into the flask to quench the reaction. The resulting mixture was filtered in vacuum and evaporated on rota vapor (Buchi). Hereafter, dissolved the residue with ethyl acetate (50 mL), and the solution was washed with 2 mol L-1 hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively, dried over anhydrous Na2SO4 and filtered. Solvent was evaporated in vacuum, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate as eluents). Finally, the samples were recrystallized from ethyl acetate / petroleum ether to afford target compounds with higher purity.Under air, add Pd (OAc) 2 (4.5mg, 0.02mmol, 10mol%), AgOAc (66.8mg, 0.4mmol, 2equiv.) To a dry 38mL sealed tube.2-hydroxypyridine (3.8mg, 0.04mmol, 20mol%), Then add Tf2NH (56.2mg, 0.2mmol, 1.0equiv) to the glove box.Finally, DCM (1.6 mL) and HFIP (0.4 mL) were sequentially added.Ethyl acrylate (26.1 muL, 0.24 mmol, 1.2 equiv) andP-trifluoromethylphenylethylamine (0.2 mmol) represented by Formula 14-1.The system was reacted at 90 C for 12h, then cooled to room temperature, the solvent and the remaining ethyl acrylate were distilled off under reduced pressure, and then dichloromethane and saturated sodium carbonate were added to the residue for extraction.The organic layer was collected, dried over anhydrous sodium sulfate, and filtered, and the solvent was distilled off under reduced pressure.The residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate / triethylamine = 11/1 / 0.4 as eluent) to obtain the product. Samples of the resulting products were noted as 14-3 and 14-4.14-3 total 38.5mg, yield 67%, 14-4 total 10.0mg, yield 13%

Molecular Weight:189.18
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:189.07653381
Monoisotopic Mass:189.07653381
Topological Polar Surface Area:26
Heavy Atom Count:13
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes