1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178483703, compound

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Reaction Steps

A solution of compound 2 (183 mg, 0.778 mmol) and Pd—C (82 mg, 0.078 mmol, 10% wt) in dry ethanol (5 mL) was purged with hydrogen gas. The reaction was stirred at room temperature over night under hydrogen atm. (balloon pressure). Then the reaction mixture was filtered through a celite pad and washed with ethanol (35 mL). The filtrate (compound 3) was treated with imidate 4 (444 mg, 1.559 mmol) and stirred over night at room temperature. The reaction was diluted with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel: 2% methanol: 98% CH2Cl2 followed by 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 followed by 5% 2M NH3 in methanol: 95% CH2Cl2, to give a greenish/yellow solid (90 mg, yield). 1H-NMR (DMSO-d6) δ 7.68 (d, J=2.7 Hz, 1H), 7.56 (dd, J=5.1, 1.2 Hz, 1H), 7.07 (dd, J=3.6, 5.1 Hz, 1H), 6.62 (s, 1H), 6.55-6.46 (m, 2H), 6.28 (s, 2H), 3.32-3.27 (m, 2H), 3.09 (t, J=6.6 Hz, 2H), 2.84 (t, J=8.1 Hz, 2H), 2.45 (t, J=6.9 Hz, 2H), 2.20 (s, 6H). ESI-MS (m/z, %): 315 (MH+, 100), 244 (29), 127 (38); ESI-HRMS calculated for C17H23N4S (MH+): calculated 315.1637, Observed: 315.1645: HPLC purity: 95.3%.

Provenance & Evidence