Hydrochloric Acid → 2-(4-Iodophenyl)ethylamine

4-Iodophenylacetonitrile (4.80 g, 19.7 mmol) was dissolved in tetrahydrofuran (25 mL) under nitrogen, and 1.0 M borane in tetrahydrofuran (29.6 mL, 29.6 mmol) was added via syringe. The reaction was heated at reflux for 1 hour, then cooled in ice and the excess borane was quenched by the addition of methanol (100 mL). When hydrogen evolution ceased, the solvents were removed under reduced pressure. The residue was dissolved in tetrahydrofuran (25 mL) and 4N HCl in dioxane (6.0 mL, 24 mmol) was added, followed by ether (75 mL). The hydrochloride salt of 4-iodophenethylamine was collected on a Buchner funnel, washed with ether (2×50 mL) and dried under reduced pressure. To generate the free base, the solid was partitioned between dichloromethane (200 mL) and 1N NaOH (100 mL). The aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated to give 4-iodophenethylamine (4.52 g) as a colorless oil.

1. temperatureThe reaction was heated
2. temperatureat reflux for 1 hour
3. temperaturecooled in ice
4. customthe excess borane was quenched by the addition of methanol (100 mL)
5. customthe solvents were removed under reduced pressure
6. dissolutionThe residue was dissolved in tetrahydrofuran (25 mL)
7. customThe hydrochloride salt of 4-iodophenethylamine was collected on a Buchner funnel
8. washwashed with ether (2×50 mL)
9. customdried under reduced pressure
10. customthe solid was partitioned between dichloromethane (200 mL) and 1N NaOH (100 mL)
11. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
12. dry with materialThe combined organic layers were dried (Na2SO4)
13. concentrationconcentrated

ORD record

ord-0b96424a88e54875af20805b5d865c26

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670376B1