Hydrochloric Acid → HCID 60155697, compound

HRID 1749844Notes

Reaction equation

HRID 1749844 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)=[C:19]([O:35][CH2:36][CH3:37])[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\[O:12][C:13]3[C:20]([CH2:21][N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([O:35][CH2:36][CH3:37])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682014HCID 86682014, compound

Product 1

HCID 60155697HCID 60155697, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-ethoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.106 g, 0.210 mmol) in methylene chloride (4 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (4 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 (4 mL), and the precipitated solid was collected by filtration. The resulting solid was washed with water, and then dried under reduced pressure to obtain (Z)-2-[(1H-indol-3-yl)methylene]-6-ethoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0653 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate (4 mL)
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe resulting solid was washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0fde7407c3fd4b85aeac5b5525f00018
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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