Water → [(1H-indol-4-yl)methyl](methyl)amine

1H-Indole-4-carbaldehyde (219 mg, 1.51 mmol) was dissolved in anhydrous methanol (7 ml). Methylamine (0.60 ml of 33% solution in ethanol, 4.82 mmol) was added and the reaction was stirred for 3 h. The solution was concentrated to an orange solid and then dissolved in anhydrous methanol (7 ml). Sodium borohydride (58.0 mg, 1.53 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 (1H-indol-4-ylmethyl)-methyl-amine (229 mg, 94%) as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ 11.03 (bs, 1H), 7.29-7.24 (m, 2H), 7.03-6.93 (m, 2H), 6.51-6.50 (m, 1H), 3.88 (s, 2H), 2.30 (s, 3H).

1. concentrationThe solution was concentrated to an orange solid
2. dissolutiondissolved in anhydrous methanol (7 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 record

ord-a37eedb925224cc38a3b24a26a73d5bd

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2