Ammonia → HCID 178456218, compound

Participants

Reaction Steps

A solution of 1-(2-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (130 mg, 0.50 mmol) in 10 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (285 mg, 1.00 mmol) and stirred at room temperature for 3 days. Argon was bubbled through the solution for 20 minutes. The solution was partitioned between CH2Cl2 (100 mL) and saturated sodium carbonate (15 mL). The organic layer was separated and the aqueous layer was extracted with an additional 50 mL CH2Cl2. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a yellow residue which was subjected to flash chromatography on silica gel using 2.5% MeOH/CH2Cl2 then 5-10% 2M NH3 in MeOH/CH2Cl2. A light orange solid was obtained (100 mg, 54.3%). 1H-NMR (DMSO-d6) δ: 7.67 (d, J=3.6 Hz, 1H), 7.55 (d, J=4.2 Hz, 1H), 7.08-7.05 (m, 1H), 6.56-6.48 (m, 3H), 6.25 (br s, 2H), 3.44 (dd, J=4.5, 14.4 Hz, 1H), 3.33-3.25 (m, 2H), 2.95 (dd, J=8.7, 13.8 Hz, 1H), 2.72-2.58 (m, 7H), 1.86-1.82 (m, 2H), 1.67 (br, 4H), 1.03 (d, J=6.3 Hz, 3H).

Provenance & Evidence