Sodium Iodide → 2-Chloro-5-[3-(3-hydroxypropylthio)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.06 g, Example 3a) and 1,8-diazabicyclo(5.4.0)undec-7-ene (0.07 ml) in 1-butanol (5 ml) was added sodium iodide (0.023 g) and 3-mecaptopropan-1-ol (0.04 ml). The reaction vessel was sealed and the mixture heated at 100° C. for 24 h. The reaction mixture was diluted with ethyl acetate and washed twice with 2M hydrochloric acid, twice with sodium hydrogencarbonate solution and once with brine. The organics were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by NPHPLC (eluting with 0-2% ethanol in dichloromethane) to leave the title compound as a white solid (0.05 g).

Provenance & Evidence