Ammonia → HCID 178483704, compound

Participants

Reaction Steps

A solution of 1-(2-(dimethylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine (900 mg, 4.10 mmol) in 25 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (2.34 g, 1.43 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was partitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (20 mL). The organic layer was separated and the aqueous layer was extracted with an additional 50 mL CH2Cl2. The combined organic layers were rinsed with water, dried over sodium sulfate, filtered and concentrated to give a dark oil which was subjected to flash chromatography on silica gel using 5% MeOH/CH2CH2then 5% 2M NH3 in MeOH/CH2C12 to give an orange solid. 1H-NMR (DMSO-d6) δ: 7.66 (d, J=3.6 Hz, 1H), 7.55 (d, J=4.8 Hz, 1H), 7.08-7.05 (m, 1H), 6.57-6.48 (m, 3H), 6.25 (brs, 2H), 3.29-3.21 (m, 4H), 2.65 (t, J=6.3 Hz, 2H), 2.39 (t, J=6.3 Hz, 2H), 2.19 (s, 6H), 1.85-1.82 (m, 2H).

Provenance & Evidence