Hydrazine hydrate (1:1) → 3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine

A solution of N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}phthalimide (119.4 g, 0.3 mole) and hydrazine hydrate (78.6 mL, 1.62 mole) in 95% ethyl alcohol (1.5 L) was heated at reflux temperature for 17.5 hours. The thick white mixture was cooled in an ice-water bath, filtered and the solid washed with ice cold 95% ethyl alcohol. The combined filtrate and washings were evaporated under reduced pressure and the residue was partitioned between 940 mL of 5% aqueous sodium hydroxide and 500 mL of dichloromethane. The aqueous phase was extracted with 500 mL of dichloromethane and the combined organic phase was extracted with 300 mL of saturated aqueous sodium chloride. The organic phase was dried, evaporated under reduced pressure and the residue was distilled under high vacuum to give 49.9 g of the title compound; bp=143°-147° C. at 0.25 mmHg.

1. temperatureat reflux temperature for 17.5 hours
2. temperatureThe thick white mixture was cooled in an ice-water bath
3. filtrationfiltered
4. washthe solid washed with ice cold 95% ethyl alcohol
5. customThe combined filtrate and washings were evaporated under reduced pressure
6. customthe residue was partitioned between 940 mL of 5% aqueous sodium hydroxide and 500 mL of dichloromethane
7. extractionThe aqueous phase was extracted with 500 mL of dichloromethane
8. extractionthe combined organic phase was extracted with 300 mL of saturated aqueous sodium chloride
9. customThe organic phase was dried
10. customevaporated under reduced pressure
11. distillationthe residue was distilled under high vacuum

ORD record

ord-c8ba84f5d8f1469bbb5bb3dc0f64257f

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04927968