Hydrochloric Acid → (1H-indol-3-yl)methylene-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one

HRID 1749837Notes

Reaction equation

HRID 1749837 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.Cl>C(Cl)Cl.O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][CH:19]=[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[C:13]=3[O:12]2)=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60155877tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

Product 1

HCID 71278753(1H-indol-3-yl)methylene-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-oneYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0305 g, 0.0664 mmol) in methylene chloride (2 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain (Z)-2-[(1H-indol-3-yl)methylene-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0220 g, 95%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-75560f0d0d0c409490d4874d28efa8b9
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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