Tetrahydrofuran → N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-methyl-1H-indole-3-carboxamide

HRID 2290201Notes

Reaction equation

HRID 2290201 reaction equation
C[C:2]1([C:11](O)=O)[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[CH2:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][NH2:22])[CH3:15].C1(N=C=NC2CCCCC2)CCCCC1.[O:38]1CCC[CH2:39]1>>[CH2:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][NH:22][C:39]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH3:11])=[O:38])[CH3:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 20231919HCID 20231919, compound

Product 1

HCID 13490821N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-methyl-1H-indole-3-carboxamide

Procedure

To a solution of 8 g of 2-methylindolecarboxylic acid and 6 g of 1-ethyl-2-pyrrolidinylmethylamine in 140 ml of tetrahydrofuran was added 9.5 g of dicyclohexylcarbodiimide, and the whole mixture was refluxed under heating for 1.5 hours. After cooling, the precipitated dicyclohexylurea was filtered off and the filtrate was concentrated. The resulting residue was crystallized with 20 ml of ethyl acetate and the crystals were filtered with suction and then recrystallized from ethyl acetate to give 10 g of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methylindole-3-carboxamide as white crystals, melting at 132°-135° C.

Workup

  1. temperaturethe whole mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated dicyclohexylurea was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was crystallized with 20 ml of ethyl acetate
  7. filtrationthe crystals were filtered with suction
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-53e8299959524619aeb59631815adc24
Source dataset
uspto-grants-1986_10
Patent number
US04616009

Reaction notes

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