Trifluoroacetic acid → HCID 12271391, compound

To a solution of N-iodosuccinamide (NIS) (4.95 g, 22 mmol) in dry acetonitrile (50 mL) was added 2-(3,4-dimethoxyphenyl)ethanamine (3.32 mL, 20 mmol) and trifluoroacetic acid (3.85 mL, 50 mmol) with stirring. The mixture was stirred at room temperature in a 250 mL round bottom flask for two hours. The acetonitrile was removed and the remaining solid was taken up in water. The water solution was treated with saturated sodium bisulfite aqueous solution until the purple color disappeared. The pH was adjusted to 8 and the aqueous solution was extracted with dichloromethane (3×50 mL) The organic layers were combined and dried over sodium sulfate. The solvent was evaporated to yield 2-(2-iodo-4,5-dimethoxyphenyl)ethanamine (4.3 g, 70%). The crude product was dried under dynamic vacuum overnight and was sufficiently pure for subsequent steps.

1. stirringThe mixture was stirred at room temperature in a 250 mL round bottom flask for two hours
2. customThe acetonitrile was removed
3. additionThe water solution was treated with saturated sodium bisulfite aqueous solution until the purple color
4. extractionthe aqueous solution was extracted with dichloromethane (3×50 mL) The organic layers
5. dry with materialdried over sodium sulfate
6. customThe solvent was evaporated

ORD record

ord-0202441a286c4d7db950922d446de677

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278959B2