Acetic Acid → 1-benzyl-N,4-dimethylpiperidin-3-amine

To a stirred solution of 1-benzyl-4-methyl-piperidin-3-one (2.3 grams, 11.5 mmol), prepared by the methods of Iorio, M. A. and Damia, G., Tetrahedron, 26, 5519 (1970) and Grieco et al., Journal of the American Chemical Society, 107, 1768 (1985), (modified using 5% methanol as a co-solvent), both references are incorporated by reference in their entirety, dissolved in 23 mL of 2 M methylamine in tetrahydrofuran was added 1.4 mL (23 mmol) of acetic acid and the resulting mixture stirred in a sealed tube for 16 hours at room temperature. Triacetoxy sodium borohydride (4.9 grams, 23 mmol) was added and the new mixture stirred at room temperature in a sealed tube for 24 h, at which time, the reaction was quenched upon addition of 1 N sodium hydroxide (50 mL). The reaction mixture was then extracted 3×80 mL with ether, the combined ether layers dried over sodium sulfate (Na2SO4) and concentrated to dryness in vacuo affording 1.7 grams (69%) of the title compound as a white solid. LRMS: 219.1 (M+1).

1. stirringthe new mixture stirred at room temperature in a sealed tube for 24 h, at which time
2. customthe reaction was quenched upon addition of 1 N sodium hydroxide (50 mL)
3. extractionThe reaction mixture was then extracted 3×80 mL with ether
4. dry with materialthe combined ether layers dried over sodium sulfate (Na2SO4)
5. concentrationconcentrated to dryness in vacuo

ORD record

ord-259dfe2331f54857a1e59f326a9ca9ae

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07250420B2