Water → [3-(4-Chlorophenyl)propyl]methylamine

Intermediate 21 (0.35 g), methylamine (2.07 ml, 2M solution in tetrahydrofuran) were stirred together in tetrahydrofuran (15 ml) for 5 min, before sodium triacetoxyborohydride (1.32 g) was added. The reaction was stirred for 18 h, before water (10 ml) was added, and the tetrahydrofuran was removed in vacuo. The resulting slurry was washed with ethyl acetate (3×50 ml), and then basified to pH 11 using sodium hydroxide (2M). The aqueous was then re-extracted with ethyl acetate (3 ×50 ml). These combined organic extracts were washed with brine (100 ml), dried over magnesium sulphate (1 g), and the solvent removed in vacuo to yield the title compound as a colourless oil (0.13 g).

1. additionwas added
2. additionwas added
3. customthe tetrahydrofuran was removed in vacuo
4. washThe resulting slurry was washed with ethyl acetate (3×50 ml)
5. extractionThe aqueous was then re-extracted with ethyl acetate (3 ×50 ml)
6. washThese combined organic extracts were washed with brine (100 ml)
7. dry with materialdried over magnesium sulphate (1 g)
8. customthe solvent removed in vacuo

ORD record

ord-6b659a6aa82d441fad472ecec662a86e

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06462042B1