Ammonia → 1-(1-Methyl-1H-indol-4-yl)ethan-1-amine

HRID 2113129Notes

Reaction equation

HRID 2113129 reaction equation
[N:1]1C=CC=C(C(N)C)C=1.[CH3:10][N:11]1[C:19]2[C:14](=[C:15]([C:20](=O)[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.N.CO.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:10][N:11]1[C:19]2[C:14](=[C:15]([CH:20]([NH2:1])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 27716881-(Pyridin-3-yl)ethan-1-amineHCID 5003444Sodium cyanoborohydrideHCID 149872881-(1-Methyl-1H-indol-4-yl)ethanone

Product 1

HCID 208032231-(1-Methyl-1H-indol-4-yl)ethan-1-amineYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared by the same procedure for preparing 1-pyridin-3-yl-ethylamine from 1-(1-methyl-1H-indol-4-yl)-ethanone (1.75 g, 10 mmol), 2 M ammonia solution in methyl alcohol (25 mL, 50 mmol, Aldrich), acetic acid (15 mL, J. T. Baker) and sodium cyanoborohydride (2.5 g, 40 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, 2 M ammonia solution in methyl alcohol/ethyl acetate 1/10) in form as light yellow oil in 48% yield (0.83 g, 4.8 mmol).

Workup

  1. customThe title compound was purified by column chromatography (silica gel, 2 M ammonia solution in methyl alcohol/ethyl acetate 1/10) in form as light yellow oil in 48% yield (0.83 g, 4.8 mmol)

Sources & evidence

ORD record
ord-a6016cc17d1f4c03a7aa9436adb94f37
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

Loading…