Dichloromethane → HCID 86753857, compound

Participants

Reaction Steps

A stirred mixture of 3-chloro-8-methoxy-4,5-dihydronaphth[1,2-c]isoxazole (2.0 g, 8.51 mmol), 4-(6-fluorobenzisoxazol-3-yl)-piperidine (2.8 g, 12.76 mmol) and K2CO3 (2.35 g, 17.02 mmol) in 10 ml of N-methylpyrrolidinone under N2 was lowered into an oil bath preheated to 150° C. The mixture was heated while stirring under N2 for 90 minutes. At that time TLC (CH2Cl2) showed no remaining starting material. The mixture was removed from the heating bath and allowed to cool to room temperature. Upon dilution of the reaction mixture with H2O, a solid precipitated which was collected, dried, dissolved in CH2Cl2 and filtered through neutral alumina. The fractions containing desired product were combined and concentrated, and the resultant solid obtained was triturated with Et2O to provide a solid, mp of 181°-183° C., homogeneous by TLC [silica, 2:1 Heptane:EtOAc, Rf=0.15]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =419, EI, 70 eV) were consistent with the structure. The yield was 1.1318 g (2.70 mmol, 31.70%).

Provenance & Evidence