ChemicalBook CAS DataBase List (1-Tosyl-1H-indol-4-yl)methanamine

(1-Tosyl-1H-indol-4-yl)methanamine synthesis

5synthesis methods

Product Name:(1-Tosyl-1H-indol-4-yl)methanamine
CAS Number:1145678-74-5
Molecular formula:C16H16N2O2S
Molecular Weight:300.38

31271-86-0
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1145678-74-5
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Yield:1145678-74-5 78%

Reaction Conditions:

with ammonia;hydrogen;Raney Nickel in methanol at 20; under 5 Torr; for 6 h;

Steps:

38.b

A mixture of 1-tosyl-1 H-indole-4-carbonitrile (0.5 g, 1.69 mmol), 5% NH₃ in methanol (5.0 mL) and Raney Nickel (0.2 g) in methanol (15.0 ml) was hydrogenated at 5 Torr for 6 h at it After completion of the reaction, the Raney Nickel was filtered off through a pad of celite under vacuum and washed with methanol (5 x 2 mL). The combined filtrates were evaporated to dryness under reduced pressure. The residue was washed with 10 % diethyl ether in pentane to yield the title compound as a white solid (0.45 g, 78 %). [¹H-NMR (CDCI₃, 300 MHz): δ 7.72-7.59 (m, 3H), 7.44-7.52 (m, 1 H), 7.33-6.72 (m, 5 H), 4.12-4.01 (m, 2H), 2.27 (s, 3H)].

References:

WO2011/76747,2011,A1 Location in patent:Page/Page column 71

98-59-9 Synthesis