1-(3-ISOPROPOXYPHENYL)METHANAMINE synthesis

Yield:-

Reaction Conditions:

with hydrogen;Raney Nickel in ethanol; under 2068.65 Torr; for 3 h;

Steps:

II.2

Step 2: (3-Isopropoxybenzyl)amine:; A 50OmL Parr bottle was flushed with argon, then 3-isopropoxybenzonitrile (32g, 198 mmol) was added and diluted with 15OmL EtOH. The reaction was charged with ~2mL of an aq. slurry of Raney Nickel, then affixed to a Parr hydrogenation apparatus. The flask was evacuated and flushed with N₂ three times before being charged with 40 psi H₂. The flask was allowed to shake for 3 hr over which time the flask was recharged to 40 psi and consumption of gas ceased. HPLC/MS showed no starting material so the catalyst was carefully filtered without drying and washed with EtOH. The filtrate was concentrated and purified on an Isco automated system affixed with a Biotage Flash 40(M) cartridge eluted with 0-5% (MeOH + 0.5M NH₃) in CH₂Cl₂ over 30 min at 40mL/min to give the product. ¹H NMR (400 MHz, CDCl₃) δ 7.24 (m, IH), 6.85 (m, 2H), 6.76 (m, IH), 4.56 (m, IH), 3.83 (s, 2H), 1.4 (bs, ~2H), 1.33 (d, J = 6.0 Hz, 6H) ppm.

References:

WO2007/11810,2007,A1 Location in patent:Page/Page column 27