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(1-benzothien-2-ylmethyl)methylamine(SALTDATA: HCl) synthesis

3synthesis methods
-

Yield:335032-47-8 99%

Reaction Conditions:

with sodium hydroxide;LiAlH4 in tetrahydrofuran;water;

Steps:

43.b Preparation of 2-(methylaminomethyl)benzothiophene

b) 2-(Methylaminomethyl)benzothiophene To a stirred suspension of N-methyl benzothiophene-2-carboxamide (10.0 g, 52 mmole) in dry THF (75 mL) under argon was added a solution of 1.0 M LiAlH4 in THF (135 mL, 135 mmole) over 15 minutes. The reaction quickly became clear and was heated at reflux for 2 days. After cooling to 0 °C the reaction was carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.1 mL), and H2O (15.3 mL). The mixture was filtered through a pad of celite and the filter pad was rinsed with Et2O (50 mL). The filtrate was concentrated to afford the title compound (9.11 g, 99%) as a pale yellow oil which solidified in the freezer: 1H NMR (400 MHz, CDCl3) δ 7.83 (d, J = 7.3 Hz, 1 H), 7.72 (d, J = 7.3 Hz, 1 H), 7.33 (m, 2 H), 7.17 (s, 1 H), 4.06 (s, 2 H), 2.53 (s, 3 H), 1.56 (br s, 1 H).

References:

EP1226138,2004,B1