Benzyl Bromide → N-benzyl-N-[[4-[(2-pyridylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine

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Reaction Steps

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.220 g, 0.390 mmol) in CH3CN (8 mL), at room temperature, was added powdered K2CO3 (0.153 g, 1.11 mmol) followed by excess benzyl bromide (0.20 mL, 1.68 mmol). After 18 hours, the reaction mixture was concentrated and the residue was partitioned between CH2Cl2 (10 mL) and water (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH) provided the desired product (0.106 g, 44%) as a white solid.

Provenance & Evidence