Benzylamine → Benzyl-(6-fluoroindan-1-ylidene)-amine

Participants

Reaction Steps

Combine 6-fluoroindan-1-one (14.57 g, 97.04 mmol) and benzylamine (10.60 mL, 97.04 mmol) in toluene (75 mL). Add p-toluenesulfonic acid monohydrate (0.923 g, 4.85 mmol). Attach a reflux condenser and heat the mixture under nitrogen to reflux over six hours, then stir at room temperature for 14 hours. Extract the mixture with ethyl acetate and water. Dry the resulting organics with magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a red oil (23.22 g, 100%). MS (ES) m/z=240 [M+1].

Provenance & Evidence