1,1'-Carbonyldiimidazole → HCID 11045735, compound

HRID 392752Notes

Reaction equation

HRID 392752 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35](C)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:12])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acidHCID 114013941-Boc-4-methylpiperazine

Product 1

HCID 11045735HCID 11045735, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indole-2-carboxylic acid (5.2 g) in THF (200 mL) was treated with carbonyldiimidazole (4.8 g) and stirred at ambient temperature for 10 min whereupon 4-methyl-piperazine-1-carboxylic acid tert-butyl ester (5.0 g) was added. The mixture was stirred at ambient temperature for 72 h and the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic portion was separated, dried over sodium sulfate and filtered, and solvent was evaporated to afford a solid. Recrystallization from hot ethanol afforded 4-(1H-Indole-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (4.2 g).

Workup

  1. additionwas added
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. customThe organic portion was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customsolvent was evaporated
  9. customto afford a solid
  10. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-62299f0dd73f47dab11d8eaa9271f525
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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