Diethylamine → 1H-indole-7-carboxylic acid diethylamide

HRID 1351933Notes

Reaction equation

HRID 1351933 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:13]([N:15]([CH2:16][CH3:17])[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)=[O:12])[CH3:14]

Participants

8

Reactant 5

HCID 8021DiethylamineHCID 8471TriethylamineHCID 742811H-Indole-7-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 545468101H-indole-7-carboxylic acid diethylamideYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1H-indole-7-carboxylic acid (0.48 g, 3 mmol), diethylamine (0.93 mL, 9 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.74 g, 9 mmol), 1-hydroxybenzotriazole (1.23 g, 9 mmol), triethylamine (1.26 mL, 12 mmol) in dimethylformamide (30 mL) is stirred at room temperature for 4 hours. The mixture is diluted with ethyl acetate, washed with 1N HCl, water, a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated brine, dried over magnesium sulfate, and concentrated to give the desired 1H-indole-7-carboxylic acid diethylamide (0.64 g, yield: 99%).

Workup

  1. washwashed with 1N HCl, water
  2. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water, and a saturated brine, dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-45744f468f2a4f2bbf4c7bb73810f3c7
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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