Hydrochloric Acid → 3-[3-(3-Phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine

Temperature

60 °C

To a solution of 6-(3-nitrophenyl)-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexan-2-one (Preparation 24, 55 mg, 0.16 mmol) in tetrahydrofuran (3 ml) under nitrogen, was added dropwise at room temperature a 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (0.81 ml, 0.81 mmol). The mixture was heated to 60° C. for 4 h. Further lithium aluminium hydride in tetrahydrofuran (1.0M, 0.3 ml, 0.3 mmol) was added, and the mixture was heated at 60° C. for 20 minutes, then cooled to room temperature. Water (30 ml) was carefully added, then the residue was acidified by the addition of 2N hydrochloric acid (5 ml), and then basified with 2N sodium hydroxide solution (6 ml). The mixture was extracted with ethyl acetate (3×50ml). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in ethanol (5 ml), Raney nickel (50 mg) was added, and the mixture was placed under an atmosphere of hydrogen (2 atm, 203 kPa) and stirred at 60° C. for 16 h. The mixture was filtered through Celite™ and concentrated in vacuo to give the title compound as a pale yellow oil (35 mg, 75%).

1. temperaturethe mixture was heated at 60° C. for 20 minutes
2. temperaturecooled to room temperature
3. extractionThe mixture was extracted with ethyl acetate (3×50ml)
4. dry with materialThe combined extracts were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in ethanol (5 ml)
8. additionRaney nickel (50 mg) was added
9. filtrationThe mixture was filtered through Celite™
10. concentrationconcentrated in vacuo

ORD record

ord-7acfe6b9ce46426982b2cf415df6f719

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1