Water → N-methyl-N-[(1-methyl-1H-indol-6-yl)methyl]amine

1-Methyl-1H-indole-6-carbaldehyde (146 mg, 0.91 mmol) was dissolved in anhydrous methanol (4 ml). Methylamine (0.35 ml of 33% solution in ethanol, 2.81 mmol) was added and the reaction was stirred for 3 h. The solution was concentrated to a yellow oil and then dissolved in anhydrous methanol (4 ml). Sodium borohydride (34.9 mg, 0.92 mmol) was added and the mixture was stirred overnight at room temperature. Water (10 ml) was added and the solution was concentrated. Sodium hydroxide (10 ml, 1N) was added and the aqueous layer was extracted with ethyl acetate (3×20 ml). Combined organic layers were dried over MgSO4, filtered and concentrated to afford methyl-(1-methyl-1H-indol-6-ylmethyl)-amine (139 mg, 87%) as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 7.44 (d, J=8.0 Hz, 1H), 7.34 (s, 1H), 7.240 (d, J=3.6, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.345 (d, J=4.0 Hz, 1H)), 3.75 (s, 3H), 3.73 (s, 2H), 2.27 (s, 3H).

1. concentrationThe solution was concentrated to a yellow oil
2. dissolutiondissolved in anhydrous methanol (4 ml)
3. stirringthe mixture was stirred overnight at room temperature
4. concentrationthe solution was concentrated
5. additionSodium hydroxide (10 ml, 1N) was added
6. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
7. dry with materialCombined organic layers were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD-Eintrag

ord-6bdb5bb388ba4bcb9a2d1a7b88f2f10b

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08450307B2