Diethyl Ether → HCID 68689093, compound

Participants

Reaction Steps

A mixture of 3-(chloromethyl)-2-(1-chloropropan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (from Isomer B, 0.16 g, 0.58 mmol), K2CO3 (0.16 g, 1.2 mmol), and benzylamine (0.075 ml, 0.67 mmol) in diglyme (1.5 ml) was heated at reflux for 6 h. After cooling to room temperature the reaction was transferred to a separatory funnel with ether and water. Extraction with ether and washing the organic layer with water (4×) and brine, and drying over MgSO4 afforded 0.15 g of crude product after evaporation of the solvent. Flash chromatography (SiO2, hexanes to 60% EtOAc in hexanes) afforded pure product (93 mg, 52% yield). MS (ESI) 307 (M+H).

Provenance & Evidence