Water → 4-(Aminomethyl)benzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

Add lithium aluminum hydride (1M solution in THF, 7.5 mL) to benzo[b]thiophene-4-carbonitrile (prepared as described in WO 0168653) (0.6 g, 3.8 mmol) at 0° C. in THF (38 mL). After 17 h at ambient temperature, cool to 0° C. and add sequentially water (1.89 mL), 2N aqueous NaOH (1.89 mL) and water (2.69 mL). Filter the solids and evaporate the filtrate to obtain the crude amine. Purify by SCX chromatography. Rinse the column with methanol, add a solution of the crude amine in methanol, wash the column with methanol and then elute with 1N ammonia in methanol. Concentrate to give the title compound (0.57 g, 93%). GC-MS m/z: 163 (M+).

Provenance & Evidence