Aluminium lithium hydride → 1-(Benzo[b]thiophen-2-yl)-N-methylmethanamine

Temperature

0 °C

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).

1. customThe reaction quickly became clear
2. temperaturewas heated
3. temperatureat reflux for 2 days
4. customwas carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.1 mL), and H2O (15.3 mL)
5. filtrationThe mixture was filtered through a pad of celite®
6. washthe filter pad was rinsed with Et2O (50 mL)
7. concentrationThe filtrate was concentrated

ORD record

ord-b3db749bb8b74c78aa6f95b7f1c54c48

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557125B2