Acetic Acid → N-(4-tert-Butylbenzyl)-N-(4-chlorobenzyl)amine

To a solution of 4-tert-butylbenzaldehyde (3.24 g, 20.0 mmol) and 4-chlorobenzylamine (2.43 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 reaction mixture was stirred at room temperature overnight. Water (10 mL) was added and the mixture was concentrated in vacuo. The residue was taken up in ethyl acetate (50 mL) and aqueous 1 M KOH (50 mL) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 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, 70 g/150 mL) with ethyl acetate (33-100% gradient) in heptane as the eluent yielded 4.31 g (75%) of white solids.

1. concentrationthe mixture was concentrated in vacuo
2. customaqueous 1 M KOH (50 mL) and the phases were separated
3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
4. dry with materialthe combined organic phase was dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customPurification on a prepacked column of silica gel (Isolute® SPE Column, 70 g/150 mL) with ethyl acetate (33-100% gradient) in heptane as the eluent

ORD record

ord-fbd67005ac154a55a2f918671b02c3ac

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07488844B2