Sodium cyanoborohydride → Benzenemethanamine, 4-fluoro-N-methoxy-

Temperature

25 °C

In an alternative procedure a solution of 4-fluorobenzaldehyde O-methyloxime (0.82 g, 5.35 mmol) in acetic acid ( 8 ml ) was treated at 10° C. with sodium cyanoborohydride (0.67 g, 10.7 mmol) added in small portions over 10 min and the resulting solution was stirred at 25° C. for 18 h. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with water and the pH was adjusted to 9 with 2 N aqueous sodium hydroxide. The aqueous phase was extracted twice with ether 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 hexane-ethyl acetate, 8:2) and distilled in vacuo to give 0.62 g (75% yield) of the title amine as a clear oil.

1. additionadded in small portions over 10 min
2. customThe solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue
3. extractionThe aqueous phase was extracted twice with ether
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 hexane-ethyl acetate, 8:2)
8. distillationdistilled in vacuo

ORD record

ord-9566c8a0c167463ea3cc97075fef2179

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777440B2