1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178511877, compound

Participants

Reaction Steps

A solution of compound 4 (0.23 g, 0.88 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.502 g, 1.76 mmol) at room temperature and was stirred for 3 hours. The mixture was diluted with saturated sodium bicarbonate solution (50 mL) and was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL) and dried (Na2SO4). The concentrated crude product was subject to flash chromatography on silica gel using 5% methanol/CH2Cl2, which resulted in a brown foam, compound 64 (0.194 g, 59%). 1H NMR (CDCl3) δ 7.66 (d, J=3.9 Hz, 1H), 7.54 (d, J=4.5 Hz, 1H), 7.06 (dd, J=3.6, 5.1 Hz, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.21 (brs, 2H), 3.57 (t, J=9.3 Hz, 4H), 3.24 (t, J=11.4 Hz, 2H), 3.65 (t, J=12.6 Hz, 2H), 2.45-2.41 (m, 6H), 1.88-1.80 (m, 2H); MS-ESI (m/z, %): 372 (11), 371 (MH+, 100), 258 (9); ESI-HRMS calculated for C20H27N4OS (MH+): Calculated: 371.1914, Observed: 371.1900.

Provenance & Evidence