Ethanol → 2-(6-Fluoro-1H-indol-3-yl)-N-[[3-(2,2,3,3-tetrafluoropropoxy)phenyl]methyl]ethanamine

Combine 6-fluorotryptamine hydrochloride (90 g, 0.419 mol) and water (900 ml). Add an aqueous solution of NaOH (2N, 230 ml) and dichloromethane (900 ml). After 1 hour, separate the organic layer, extract the aqueous layer with dichloromethane, combine the organic layers, wash water, dry over MgSO4, and evaporate to a residue. Combine the residue and toluene (200 ml) and evaporate to give 78.45 g of a brown oil. Combine the above 78.5 g with another 41.4 g batch to provide 6-fluorotryptamine. Combine 6-fluorotryptamine (119.85) and ethanol (3.325 L), add 2,2,3,3-tetrafluoropropoxybenzaldehyde (176 g, 0.745 moles, 1.2 equiv.) and 150 g of molecular sleve 3 Å. Heat to reflux. After 2 hours, cool to RT room temperature and add NaBH4 (35.2 g, 0.93 mol, 1.5 equiv.). After 1 hour, filter through celite and wash with 500 ml of ethanol. Evaporate the filtrate under reduced pressure to give an oily residue. Partition the residue between water and dichloromethane. Separate the layers, extract the aqueous later with dichloromethane, combine organic layers, wash with brine and dry over MgSO4. Filter and evaporate under reduced pressure to give the title compound.

1. temperatureHeat to reflux
2. waitAfter 1 hour
3. filtrationfilter through celite
4. washwash with 500 ml of ethanol
5. customEvaporate the filtrate under reduced pressure
6. customto give an oily residue
7. customPartition the residue between water and dichloromethane
8. customSeparate the layers
9. extractionextract the aqueous later with dichloromethane
10. washwash with brine
11. dry with materialdry over MgSO4
12. filtrationFilter
13. customevaporate under reduced pressure

ORD 기록

ord-1ee24821430c4021b582decf0c09565b

출처 데이터셋

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07157488B2