Hydrazine hydrate (1:1) → Benzenepentanamine

Hydrazine monohydrate (0.36 g, 7.2 mmol) was added to a solution of 2-(5-phenylpentyl)isoindoline-1,3-dione (0.68 g, 2.3 mmol) in 25 mL of EtOH. The solution was stirred under reflux for 5 hrs and then cooled to room temperature. The white precipitate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in a 1N solution of NaOH (80 mL) and extracted with chloroform (3×70 mL). The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (solid deposition with TEA, eluent: 20% MeOH in dichloromethane with 1% of TEA) to afford the title compound (0.28 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3): 1.37-1.48 (m, 2H), 1.58-1.72 (m, 4H), 2.57-2.69 (m, 2H), 3.29 (t, J=6.70 Hz, 2H), 7.13-7.24 (m, 3H), 7.26-7.34 (m, 2H).

1. temperatureunder reflux for 5 hrs
2. customThe white precipitate was removed by filtration
3. concentrationthe filtrate was concentrated under reduced pressure
4. dissolutionThe residue was dissolved in a 1N solution of NaOH (80 mL)
5. extractionextracted with chloroform (3×70 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. customthe solvent was removed under reduced pressure
9. customThe crude was purified by column chromatography

ORD record

ord-68be55fa81024c86b66ce29e7064df47

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428465B2