Dichloromethane → HCID 65275388, compound

Participants

Reaction Steps

A mixture of 4-piperidinylmethanol (115 mg, 1 mmol), 5-bromo-3-(1-methylethyl)-1,2,4-thiadiazole (Example 182, Step 6, 207 mg, 1 mmol), triethylamine (0.42 mL, 3 mmol) and CH2Cl2 (3 mL) was stirred at ambient temperature overnight. The mixture was charged with additional 4-piperidinylmethanol (58 mg, 0.5 mmol) and was stirred at ambient temperature for 3 h. The mixture was charged with water, and extracted with CH2Cl2. The organics were dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 to give 159 mg (66%) of {1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-4-piperidinyl}methanol as a golden oil. 1H NMR (400 MHz, CDCl3): δ 3.98-3.88 (m, 2H), 3.54 (d, 2H, J=6.3 Hz), 3.20-3.05 (m, 2H), 3.02 (septet, 1H, J=6.9 Hz), 1.90-1.80 (m, 2H), 1.82-1.70 (m, 1H), 1.42-1.25 (m, 8H); LRMS (ESI), m/z 242 (M+H).

Provenance & Evidence