Phenethylamine → HCID 68683946, compound

Temperature

50 °C

To a solution of N-(5-bromopentyl)phthalimide (5 g, 16.9 mmol) in ACN (50 mL) was added N-benzylmethylamine (2.04 g, 16.9 mmol), followed by DIPEA (2.93 mL, 16.9 mmol). The reaction mixture was stirred at 50° C. for 3 hours and then the solvent was removed in vacuo. The residue was dissolved in DCM (100 mL), washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in MeOH (100 mL) and hydrogenated to remove the benzyl group using palladium on activated carbon (1 g, 10 wt. % (dry basis)) as a catalyst under a hydrogen gas balloon at room temperature overnight. The mixture was filtered through Celite and the solvent was removed in vacuo to yield 4.2 g of the title intermediate as a solid.

1. customthe solvent was removed in vacuo
2. dissolutionThe residue was dissolved in DCM (100 mL)
3. washwashed with brine (100 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in MeOH (100 mL)
8. customhydrogenated to remove the benzyl group
9. customat room temperature
10. customovernight
11. filtrationThe mixture was filtered through Celite
12. customthe solvent was removed in vacuo

ORD record

ord-2faa8543642e46a19f5fae9640505fb5

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569588B2