Phthalimide → 3-(4-Chlorophenyl)propan-1-amine

Temperature

80 °C

The potassium salt of phthalimide (4.4 g, 24 mmol) was dissolved in DMF (20 ml) and 1-chloro-4-(3-bromopropyl)benzene (4.67 g, 20 mmol) was added. The mixture was stirred at 80° C. for 16 hours. Water (50 ml) and DCM (50 ml) were added, the phases were separated and the aqueous phase extracted with DCM (2×50 ml). The combined organic phases were washed with sodium hydroxide (0.2 M, 50 ml), dried (magnesium sulphate), filtered and concentrated in vacuo. Ethanol (75 ml) and hydrazine hydrate (2 equiv.) were added and the mixture was heated to reflux for 2 hours. After cooling the mixture was filtrated and the filter cake washed with DCM (2×50 ml). The filtrate and washings were evaporated and dissolved in ethyl acetate (40 ml). Washing of the organic phase with sodium hydroxide (0.4 M, 2×25 ml) and water (2×25 ml) followed by drying (magnesium sulphate), filtration and evaporation gave 3-(4-chlorophenyl)propylamine.

1. customthe phases were separated
2. extractionthe aqueous phase extracted with DCM (2×50 ml)
3. washThe combined organic phases were washed with sodium hydroxide (0.2 M, 50 ml)
4. dry with materialdried (magnesium sulphate)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. temperaturethe mixture was heated
8. temperatureto reflux for 2 hours
9. temperatureAfter cooling the mixture
10. filtrationwas filtrated
11. washthe filter cake washed with DCM (2×50 ml)
12. customThe filtrate and washings were evaporated
13. dissolutiondissolved in ethyl acetate (40 ml)
14. washWashing of the organic phase with sodium hydroxide (0.4 M, 2×25 ml) and water (2×25 ml)
15. customby drying
16. filtration(magnesium sulphate), filtration and evaporation

ORD record

ord-8fcf98960afe419ea1234aa1b67f13de

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1