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

1-Methyl-1H-indole-5-carbaldehyde (338 mg, 2.13 mmol) was dissolved in anhydrous methanol (10 ml). Methylamine (0.80 ml of 33% solution in ethanol, 6.43 mmol) was added and the reaction was stirred for 3 h. The solution was concentrated to a brown oil and then dissolved in anhydrous methanol (10 ml). Sodium borohydride (83.0 mg, 2.19 mmol) was added and the mixture was stirred overnight at room temperature. Water (4 ml) was added and the solution was concentrated. Sodium hydroxide (8 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-5-ylmethyl)-amine (167 mg, 45%) as an orange oil: 1H NMR (400 MHz, DMSO-d6) δ 7.44 (s, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.261 (d, J=3.2 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 6.345 (d, J=4.0 Hz, 1H), 3.75 (s, 3H), 3.70 (s, 2H), 2.25 (s, 3H).

1. concentrationThe solution was concentrated to a brown oil
2. dissolutiondissolved in anhydrous methanol (10 ml)
3. stirringthe mixture was stirred overnight at room temperature
4. concentrationthe solution was concentrated
5. additionSodium hydroxide (8 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 record

ord-00c2ad85f56b4055a48316a99d331c20

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2