Aluminium lithium hydride → (3-ethyl-1H-indol-2-yl)-N-methylmethanamine

HRID 1362435Notes

Reaction equation

HRID 1362435 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]([NH:14][CH3:15])=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCOCC1>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:12][NH:14][CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 592775313-ethyl-N-methyl-1H-indole-2-carboxamide

Product 1

HCID 59277537(3-ethyl-1H-indol-2-yl)-N-methylmethanamineYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-ethyl-N-methyl-1H-indole-2-carboxamide (970 mg, 4.80 mmol) in dioxane was added slowly to an ice-cooled solution of lithium aluminium hydride (273 mg, 72 mmol) in dioxane (10 mL). The mixture was stirred at reflux overnight. Excess lithium aluminium hydride was quenched with 15% NaOH (2 mL) and the mixture separated. The aqueous phase was washed twice with ethyl acetate and the combined organic phases dried to afford the title compound (550 mg, 61%). 1H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 7.42 (d, J=8 Hz, 1H), 7.25 (d, J=7.6 Hz, 1H), 7.00 (t, J=7.2 Hz, 1H), 6.89 (t, J=7.2 Hz, 1H), 3.75 (s, 2H), 2.66 (q, J=7.5 Hz, 2H), 2.27 (s, 3H), 1.14 (t, J=7.6 Hz, 3H).

Workup

  1. temperatureat reflux overnight
  2. customExcess lithium aluminium hydride was quenched with 15% NaOH (2 mL)
  3. customthe mixture separated
  4. washThe aqueous phase was washed twice with ethyl acetate
  5. customthe combined organic phases dried

Sources & evidence

ORD record
ord-0255ac40f111465eba9db5533b3320ab
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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