Chloroacetone → HCID 66970969, compound

Participants

Reaction Steps

2-(1-((1S,2R,4R)-Bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)phenol (compound no. 229) (27.0 mg, 0.1 mmol) was dissolved in DMF (0.5 mL) and treated with K2CO3 (100 mg, 0.72 mmol) followed by the 1-chloropropan-2-one (19 mg, 0.4 mmol) and Nal (100 mg, 0.66 mmol) and the reaction was allowed to stir at room temperature for 48 h. The crude reaction mixture was filtered, diluted with DMSO to 1 mL and purified by LC/MS (10-99 CH3CN—H2O gradient with 0.03% TFA, 9 minute) to provide 1-(2-(1-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)phenoxy)propan-2-one (compound no. 53) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 327.0 [M+H]+, retention time 2.32 min.

Provenance & Evidence