N,N-Dimethylethylenediamine → HCID 4972539, compound

HRID 1729017Notes

Reaction equation

HRID 1729017 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.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH2:17]>CN(C)C=O>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH: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]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 742811H-Indole-7-carboxylic acid

Product 1

HCID 4972539HCID 4972539, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-7-carboxylic acid (3.20 g, 0.020 mole) was dissolved in 50 ml of dimethylformamide (DMF) and 3.3 g (0.020 mole) of N,N'-carbonyldiimidazolewas added. After stirring for 2 hours at room temperature, 2.0 g (0.023 mole) of N,N-dimethylethylenediamine was added, and stirring was continuedfor an additional 1 hour. At the end of this time the solvent was removed at a pressure of 0.1 mm Hg (50° C.) and the remaining residue was triturated with a minimum of H2O and the crude product was filtered off and dried and concentrated to give a solid. Recrystallization from ether-pentane gave 2.20 g of N-[2-(dimethylamino)ethyl]-1H-indole-7-carboxamide (48%), m.p. 100°-102° C.

Workup

  1. addition3.3 g (0.020 mole) of N,N'-carbonyldiimidazolewas added
  2. stirringstirring
  3. waitwas continuedfor an additional 1 hour
  4. customAt the end of this time the solvent was removed at a pressure of 0.1 mm Hg (50° C.)
  5. customthe remaining residue was triturated with a minimum of H2O
  6. filtrationthe crude product was filtered off
  7. customdried
  8. concentrationconcentrated
  9. customto give a solid
  10. customRecrystallization from ether-pentane

Sources & evidence

ORD record
ord-68989ecee1064471b500b94451a16af8
Source dataset
uspto-grants-1994_07
Patent number
US05330986

Reaction notes

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