Water → (1-ethyl-1H-indol-4-yl)-N-methylmethanamine

1-Ethyl-1H-indole-4-carbaldehyde (2.40 mg, 13.8 mmol) was dissolved in anhydrous methanol (62 mL). Methylamine (6.00 mL of 33% solution in ethanol, 48.2 mmol) was added and the reaction was stirred for 3 h. The solution was concentrated to a greenish brown oil and then dissolved in anhydrous methanol (62 mL). Sodium borohydride (539 mg, 14.3 mmol) was added and the mixture was stirred overnight at room temperature. Water (90 mL) was added and the solution was concentrated. Sodium hydroxide (15 mL, 1N) was added and the aqueous layer was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound ((1-ethyl-1H-indol-4-yl)-N-methylmethanamine) (2.36 g, 91%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.33-7.30 (m, 2H), 7.10-6.97 (m, 2H), 6.52 (d, J=3.0 Hz, 1H), 4.17 (q, J=7.2 Hz, 2H), 3.88 (s, 2H), 2.30 (s, 3H), 1.33 (t, J=7.2 Hz, 3H).

1. concentrationThe solution was concentrated to a greenish brown oil
2. dissolutiondissolved in anhydrous methanol (62 mL)
3. stirringthe mixture was stirred overnight at room temperature
4. concentrationthe solution was concentrated
5. additionSodium hydroxide (15 mL, 1N) was added
6. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
7. dry with materialCombined organic layers were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-95bd77bbb39443e59fac8cb4d968e226

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2