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

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.

1. concentrationthe reaction mixture was concentrated
2. customthe residue was partitioned between CH2Cl2 (10 mL) and water (5 mL)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with CH2Cl2 (2×10 mL)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. concentrationconcentrated
7. customPurification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH)

ORD record

ord-5096eb010d7c49cdaccdb9cc1ff791e4

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183273B2