Water → 2-(4-Chlorophenoxy)-N-methylethan-1-amine

To a stirred solution of Intermediate 19 (0.84 g) in tetrahydrofuran (30 ml) at 0° C. was added lithium aluminium hydride (0.64 g). The reaction was stirred at room temperature for 3 h, followed by reflux for 2 h. On cooling water (0.64 ml), aqueous sodium hydroxide (15%, 0.64 ml) and water (1.9 ml) were added. The precipitates were removed by filtration and the filtrate diluted with ethyl acetate (30 ml) and extracted with aqueous hydrochloric acid (2M, 2×30 ml). The aqueous layer was basified to pH 12 with aqueous sodium hydroxide (2M), and extracted with methanol/dichloromethane (10%, 2×50 ml). The combined organic extracts were washed with brine (40 ml) dried over magnesium sulphate (2 g) and the solvent removed in vacuo to yield the title compound as a pale yellow oil (0.32 g).

1. temperatureby reflux for 2 h
2. additionwere added
3. customThe precipitates were removed by filtration
4. additionthe filtrate diluted with ethyl acetate (30 ml)
5. extractionextracted with aqueous hydrochloric acid (2M, 2×30 ml)
6. extractionextracted with methanol/dichloromethane (10%, 2×50 ml)
7. washThe combined organic extracts were washed with brine (40 ml)
8. dry with materialdried over magnesium sulphate (2 g)
9. customthe solvent removed in vacuo

ORD record

ord-9aad7d80f2bc4f0fbff9e88662ace198

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06462042B1