Acetic Acid → HCID 43215597, compound

To a solution of 2,4-difluorobenzylamine (2.84 g, 20.0 mmol) and cyclohexanecarbaldehyde (2.60 mL, 20.0 mmol) in methanol (100 mL) were added acetic acid (4.6 mL, 80 mmol) and sodium cyanoborohydride (1.51 g, 24.0 mmol) and the solution was stirred at room temperature for three days. Water (10 mL) was added and the mixture was concentrated in vacuo. The residue was diluted with aqueous 1 M KOH (125 mL) and ethyl acetate (100 mL) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 mL) and the combined organic phase was dried over Na2SO4 and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 50 g Si/150 mL) with ethyl acetate (33-100% gradient) in heptane as the eluent yielded 2.40 g (50%) of white solids.

1. concentrationthe mixture was concentrated in vacuo
2. additionThe residue was diluted with aqueous 1 M KOH (125 mL) and ethyl acetate (100 mL)
3. customthe phases were separated
4. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
5. dry with materialthe combined organic phase was dried over Na2SO4
6. concentrationconcentrated in vacuo
7. customPurification on a prepacked column of silica gel (Isolute® SPE Column, 50 g Si/150 mL) with ethyl acetate (33-100% gradient) in heptane as the eluent

ORD record

ord-bad72cde934a4d76967768efe246f6a7

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07488844B2