p-Fluorophenethylamine → N-(4-fluorophenethyl)-2,2-dimethoxyethanamine

To a solution of 4-fluorophenethylamine (2.00 mL, 15.0 mmol) and dimethoxyacetaldehyde (60% solution in water, 2.53 mL, 16.83 mmol) in tetrahydrofuran (100 mL) was added sodium triacetoxyborohydride (4.28 g, 20.20 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 16 hours. The reaction was quenched by the addition of saturated sodium bicarbonate (50 mL). The mixture was extracted with ethyl acetate (3×100 mL) and the combined organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography eluted with ethyl acetate/hexane to afford N-(4-fluorophenethyl)-2,2-dimethoxyethanamine as a colorless oil in 52% yield (1.78 g): 1H NMR (300 MHz, CDCl3) δ 7.14-7.10 (m, 2H), 6.97-6.91 (m, 2H), 4.43-4.40 (m, 1H), 3.35 (s, 6H), 2.89-2.81 (m, 2H), 2.76-2.71 (m, 4H); MS (ES+) m/z 228.2 (M+1).

1. customThe resulting reaction mixture
2. customThe reaction was quenched by the addition of saturated sodium bicarbonate (50 mL)
3. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
4. dry with materialthe combined organic solution was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by column chromatography
8. washeluted with ethyl acetate/hexane

ORD record

ord-8111a44ba81e47098170dff6b735158d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293768B2