m-Chloroperbenzoic acid → HCID 6481412, compound

HRID 2416663Notes

Reaction equation

HRID 2416663 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].CO[C:13]([C:15]1[C:16]2[CH:17]=[CH:18][NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14].[C:24]([N:32]1[CH2:37][CH2:36][N:35]([CH2:38]C#N)[CH2:34][CH2:33]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=C(Cl)C=C(C(OO)=[O:49])C=1>C1COCC1>[C:24]([N:32]1[CH2:37][CH2:36][N:35]([C:38](=[O:49])[C:13]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][NH:19]3)=[O:14])[CH2:34][CH2:33]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2733668methyl 1H-indole-4-carboxylateHCID 219917634-Benzoyl-1-piperazineacetonitrile

Product 1

HCID 6481412HCID 6481412, compoundYield 28,518.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaHMDS (1.3 mL of a 1.0 M in THF solution, 1.3 mmol) was added to a stirring solution of 1H-indole-4-carboxylic acid methyl ester (0.048 g, 0.27 mmol) and (4-benzoyl-piperazin-1-yl)-acetonitrile (63 mmol, 0.27 mmol) in THF (3 mL) and the reaction mixture was stirred overnight. mCPBA (0.01 g of 77% max., 0.43 mmol) was added to the reaction mixture, stirred 1 d, and the solution was partitioned between brine (15 mL) and EtOAc (3×10 mL). The combined organic layers were dried (MgSO4), filtered, concentrated and purified using Shimadzu automated preparative HPLC System to give 1-(4-benzoyl-piperazin-1-yl)-2-(1H-indol-4-yl)-ethane-1,2-dione (0.028 mg, 77 mmol, 29%) as a yellow solid: MS m/z: (M+H)+ calcd for C21H19N3O3:362.14; found 362.09. HPLC retention time: 1.13 minutes (column A).

Workup

  1. stirringstirred 1 d
  2. customthe solution was partitioned between brine (15 mL) and EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-fb8d5fb4789a47be8c5653a3635f16d0
Source dataset
uspto-grants-2004_11
Patent number
US06825201B2

Reaction notes

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