Water → n-Methyl-1-(1-methyl-1h-indol-5-yl)methanamine

N-Methylindole-5-carbaldehyde (800 mg, 5.1 mmol) was dissolved in anhydrous methanol (15 mL). Methylamine (7.15 mL of 2M solution in methanol, 15.3 mmol) was added and the reaction was stirred for 3 hr. The solution was concentrated to a yellow oil and then dissolved into anhydrous methanol (15 mL). Sodium borohydride (194 mg, 5.1 mmol) was added and the mixture was stirred overnight. Water (1 mL) was added and the solution was concentrated to an orange oil. Sodium hydroxide (5 mL, 1N) was added and the product was extracted with ethyl acetate (3×20 mL), dried over MgSO4 and concentrated to afford the title compound as an orange oil (885 mg, 100%). 1H NMR (200 MHz, CDCl3) δ 7.57 (s, 1H), 7.35-7.11 (m, 3H), 6.51 (d, J=2.9 Hz, 1H), 3.85 (s, 2H), 3.79 (s, 3H), 2.48 (s, 3H).

1. concentrationThe solution was concentrated to a yellow oil
2. dissolutiondissolved into anhydrous methanol (15 mL)
3. stirringthe mixture was stirred overnight
4. concentrationthe solution was concentrated to an orange oil
5. additionSodium hydroxide (5 mL, 1N) was added
6. extractionthe product was extracted with ethyl acetate (3×20 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD-Eintrag

ord-6822850dad1b4f67aceff249dd8bc064

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07879872B2