Piperidine → 4-Piperidin-1-ylindan-1-one O-methyloxime

Participants

Reaction Conditions

Reaction Steps

4-Bromoindan-1-one O-methyloxime (6.40 g, 26.7 mmol) was added to a mixture of piperidine (2.72 g, 31.9 mmol), sodium tert-butoxide (3.84 g, 40.0 mmol), Pd2(dba)3 (0.74 g, 0.81 mmol) and BINAP (1.49 g, 2.39 mmol) in dioxane (50 mL) under nitrogen atmosphere. The stirred mixture was heated at 170° C. for 5 minutes on the microwave. After cooling to ambient temperature, the reaction mixture was filtered through celite, then silica gel with 25% ethyl acetate in hexane. The filtrate was concentrated to a brown oil and chromatographed on silica gel with 4% ethyl acetate in hexane. Obtained 4-piperidin-1-ylindan-1-one O-methyloxime (4.33 g, 66%) as an orange oil. MS (ESI) m/z: 245.00 [M+H]+. 1H NMR (DMSO-d6) □: 1.55 (m, 2H), 1.64 (m, 4H), 2.79 (m, 2H), 2.91 (m, 6H), 3.87 (s, 3H), 6.94 (dd, 1H), 7.19 (m, 2H).

Provenance & Evidence