Methylamine → (1H-indol-7-ylmethyl)(methyl)amine

A solution of 7-formyl-1H-indole (0.23 g, 1.6 mmol) in methanol (10 mL) was added with a 40% solution of methylamine in methanol (0.6 mL, 6.4 mmol), and the mixture was stirred at room temperature for 1 hour. Then, the mixture was added portionwise with sodium borohydride (0.060 g, 4.8 mmol), and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, then the residue was added with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5)) to obtain 1-(1H-indole-7-yl)-N-methylmethanamine (0.23 g, 89%).

1. stirringthe mixture was stirred at room temperature for 3 hours
2. customThe solvent was evaporated under reduced pressure
3. additionthe residue was added with ethyl acetate
4. washthe organic layer was washed successively with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5))

ORD record

ord-8e8493c2f9fc45f1a7ce5f6c5cfcebd2

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156827B2