Sulfuric Acid → HCID 524516, compound

Temperature

100 °C

To a solution of 100 g of 1-methylindole in absolute ethanol in a 600 mL autoclave, 5 g of PtO2 and 10 mL of H2SO4 were added. The mixture was sealed and pressurized with hydrogen to 1500 psig. The reaction mixture was heated at 100° C. overnight while stirring at about 400 rpm. The reaction mixture was pressurized again to 1500 psig and heated at 100° C. for several more hours. The reaction mixture was cooled and filtered to remove the catalyst. The filtrate was concentrated on a rotary evaporator to remove ethanol. The residue was neutralized with sodium hydroxide solution and left to stir at room temperature for about 30 minutes. The solution was transferred to a reparatory funnel and extracted with diethyl ether. The ether layer was dried over anhydrous MgSO4, filtered and concentrated at reduced pressure on a rotary evaporator to give 93.0 g of the product, 1-methyl-octahydroindole, as a yellow oil. The product was confirmed by NMR.

1. customThe mixture was sealed
2. temperatureheated at 100° C. for several more hours
3. temperatureThe reaction mixture was cooled
4. filtrationfiltered
5. customto remove the catalyst
6. concentrationThe filtrate was concentrated on a rotary evaporator
7. customto remove ethanol
8. waitleft
9. stirringto stir at room temperature for about 30 minutes
10. customThe solution was transferred to a reparatory funnel
11. extractionextracted with diethyl ether
12. dry with materialThe ether layer was dried over anhydrous MgSO4
13. filtrationfiltered
14. concentrationconcentrated at reduced pressure on a rotary evaporator

ORD record

ord-9e7ce3e67a144eb4a9395ad320494bd2

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056311B2