Potassium Hydroxide → HCID 59454982, compound

8,9-Dichloro-5-(2-hydroxy-2-(pyridin-4-yl)propyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (500 mg, 1.2 mmol) was dissolved in thionylchloride (5 mL) and stirred at RT for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methyl-2-pyrrolidone (5 mL) and the solution was stirred for 5 min. at RT. Powdered KOH (482 mg, 8.5 mmol) was added and the reaction mixture was heated at 100° C. for 1 h. The progress of reaction was monitored by TLC and NMR. Upon completion, the reaction mixture was cooled at RT, diluted with water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and the residue purified by HPLC. 1H NMR (CD3OD, formate salt) δ (ppm): 8.60 (d, 2H), 7.70 (d, 2H), 7.30 (m, 2H), 7.18 (d, 1H), 4.60 (m, 2H), 3.40 (m, 2H), 3.10 (m, 2H), 2.90 (s, 3H), 2.0 (s, 3H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in N-methyl-2-pyrrolidone (5 mL)
3. stirringthe solution was stirred for 5 min. at RT
4. temperaturethe reaction mixture was heated at 100° C. for 1 h
5. customThe progress of reaction
6. temperatureUpon completion, the reaction mixture was cooled at RT
7. extractionextracted with EtOAc
8. washThe organic layer was washed with water
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customthe residue purified by HPLC

ORD record

ord-bcaf8394a25c48918e8b00e845601e39

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906925B2