1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 63719141, compound

HRID 20976

Reaction equation

HRID 20976 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>CN(C=O)C.O>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)=[O:12])[CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 742801H-Indole-5-Carboxylic AcidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 63719141HCID 63719141, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Indole-5-carboxylic acid (4.09 g, 25.4 mmol) was dissolved in DMF (200 mL), and the solution was added with EDCI (9.74 g, 50.8 mmol) and HOBT monohydrate (1.95 g, 12.7 mmol) under ice-cooling, followed by stirring at the same temperature for 10 minutes. Then, the reaction mixture was added with N-methylpiperazine (8.45 mL, 76.2 mmol), followed by stirring at room temperature for 3.7 hours. The reaction mixture was added with water and extracted with ethyl acetate and chloroform. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/0, 90/10) to obtain 5-(4-methylpiperazin-1-ylcarbonyl)indole (5.81 g, yield 94%).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3.7 hours
  3. extractionextracted with ethyl acetate and chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by flash column chromatography (chloroform/methanol=100/0, 90/10)

Sources & evidence

ORD record
ord-4e2548b5d63b4686a021a37ae1754841
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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