4-(2-(Piperidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178511901, compound

Participants

Reaction Steps

A suspension of 4-(2-(piperidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.90 g, 3.24 mmol) and methyl thiophene-2-carbimidothioate hydroiodide (1.85 g, 6.49 mmol) was stirred at room temperature overnight (16 hours) under an argon atmosphere. The reaction was concentrated, and the residue was partitioned between saturated sodium bicarbonate solution (50 mL) and dichloromethane (25 mL). After stirring for an hour, the mixture was poured into a separatory funnel. The organic layer was removed, and the aqueous layer was extracted into dichloromethane (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was subjected to column chromatography on silica gel (2:98 to 5:95 MeOH:CH2Cl2 followed by 5:95 (2M NH3 in MeOH):CH2Cl2) to give compound 14 as yellow solid (0.288 g, 23%). 1H-NMR (DMSO-d6) δ 7.69 (d, J=3.3 Hz, 1H), 7.57 (d, J=4.5 Hz, 1H), 7.09-7.06 (m, 1H), 6.67 (d, J=8.7 Hz, 1H), 6.52-6.47 (m, 2H), 6.39 (brs, 2H), 3.56-3.53 (m, 2H), 3.39-3.33 (m, 2H), 3.03-3.01 (m, 2H), 2.45-2.39 (m, 6H), 1.49-1.48 (m, 4H), 1.39-1.38 (m, 2H); ESI-MS (m/z, %): 387 (MH+, 77), 276 (46), 194 (100).

Provenance & Evidence