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ChemicalBook CAS DataBase List (4-(ethylsulfonyl)phenyl)methanamine hydrochloride

(4-(ethylsulfonyl)phenyl)methanamine hydrochloride synthesis

5synthesis methods
-

Yield:98959-89-8 531 mg

Reaction Conditions:

with ammonia;hydrogen in methanol;water; under 3102.97 Torr; for 1 h;

Steps:

5 Step 5: (4-(Ethylsulfonyl)phenyl)methanamine hydrochloride

To a stirred solution of 4-(ethylsulfonyl)benzonitrile (Step 4 intermediate) (1.0 g, 5.12 mmol) in methanol (30 mL) was added Raney nickel (500 mg) and aqueous ammonia (2.0 mL) at RT. The mixture was subjected to hydrogenation in a Parr apparatus under 60 psi hydrogen pressure for 1 h. The reaction mixture was filtered through celite bed and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography. The free base was stirred with hydrochloric acid in ethyl acetate to yield 513 mg of the desired product as HC1 salt. NMR (300 MHz, DMSO-Je) δ 1.09 (t, = 7.5 Hz, 3H), 3.32 (q, = 7.5 Hz, 2H), 4.15 (s, 2H), 7.76 (d, = 7.2 Hz, 2H), 7.93 (d, = 8.4 Hz, 2H), 8.50 (br s, 2H); ESI-MS (m/z) 200 (M+H)+.

References:

WO2018/116285,2018,A1 Location in patent:Page/Page column 20; 22-23