Water → 1-(1H-indol-5-yl)-N-methylmethanamine

Indole-5-carbaldehyde (1.0 g, 6.9 mmol) was dissolved in anhydrous methanol (15 mL). Methylamine (9.9 mL of 2M solution in methanol, 19.8 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 (20 mL). Sodium borohydride (262 mg, 6.9 mmol) was added and the mixture was stirred overnight. Water (1 mL) was added and the solution was concentrated. 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 a brown oil (980 mg, 91%). 1H NMR (200 MHz, CDCl3) δ 8.60 (s, 1H), 7.56 (s, 1H), 7.35-7.15 (m, 3H), 6.55 (m, 1H), 3.85 (s, 2H), 2.49 (s, 3H).

1. concentrationThe solution was concentrated to a yellow oil
2. dissolutiondissolved into anhydrous methanol (20 mL)
3. stirringthe mixture was stirred overnight
4. concentrationthe solution was concentrated
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 record

ord-27a377220e3141c9afd42a820d85f95f

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790709B2