Potassium Carbonate → N-({4-[4-(4-chlorobutoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)pyridin-2-amine

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4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol (220 mg, 0.775 mmol), 1-bromo-4-chlorobutane (146 mg, 0.852 mmol) and potassium carbonate (118 mg, 0.852 mmol) were stirred in DMF (1 ml) at 60° C. for 24 hours until complete. Reaction was partitioned between ethyl acetate (50 ml) and water (75 ml). The organic layer was separated and washed further with water (2×30 ml), then dried over sodium sulphate, filtered and concentrated in vacuo. The crude compound was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 98:2:0.2 by volume) to give the title compound (184 mg, 63%) as a yellow solid. LRMS APCI+ m/z 375 [MH]+.

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