Hydrochloric Acid → Benzenemethanamine, 4-fluoro-N-methoxy-

A solution of 4-fluorobenzaldehyde-O-methyloxime (93.2 mmol) in dichloromethane (150 ml) was treated with sodium cyanoborohydride (9.18 g, 0.146 mol) followed by 120 ml of 2 N hydrochloric acid in methanol added dropwise over 30 minutes. After 96 h at 22° C., the solvent was evaporated under reduced pressure, the residue was slurried with water and adjusted to pH 9 with 2 N aqueous sodium hydroxide. The aqueous phase was extracted twice with dichloromethane and the combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residual oil was chromatographed on silica gel (elution, toluene-ethyl acetate 0-10%) and gave 5.92 g (41% yield) of the title amine as a clear oil. 1H NMR 400 MHz (CDCl3) δ (ppm): 3.49 (3H, s), 4.01 (2H, s), 5.69 (1H, broad s), 7.01 (2H, m), 7.31 (2H, m). The hydrochloride salt was obtained as a white solid: mp 170-171° C. Anal. calcd for C8H10FNO—HCl: C, 50.14; H, 5.78; N, 7.31. Found: C, 50.31; H, 5.80; N, 7.26

1. additionadded dropwise over 30 minutes
2. customthe solvent was evaporated under reduced pressure
3. extractionThe aqueous phase was extracted twice with dichloromethane
4. washthe combined organic extracts were washed with brine
5. dry with materialdried (magnesium sulfate)
6. concentrationconcentrated under reduced pressure
7. customThe residual oil was chromatographed on silica gel (elution, toluene-ethyl acetate 0-10%)

ORD record

ord-13bd73de2c35454ba938bd4d6d6993f4

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06890942B2