Hydrochloric Acid → HCID 60155698, compound

HRID 1749846Notes

Reaction equation

HRID 1749846 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][CH2:37][CH3:38])[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][CH2:37][CH3:38])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682015HCID 86682015, compound

Product 1

HCID 60155698HCID 60155698, compoundYield 53.9%

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-6-propoxy-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0705 g, 0.136 mmol) in methylene chloride (7 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (7 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 (14 mL), and the precipitated solid was collected by filtration. The resulting solid was washed with water, and then further washed with acetonitrile to obtain (Z)-2-[(1H-indol-3-yl)methylene]-7-(piperazin-1-ylmethyl)-6-propoxybenzofuran-3(2H)-one (0.0306 g, 53%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate (14 mL)
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe resulting solid was washed with water
  5. washfurther washed with acetonitrile

Sources & evidence

ORD record
ord-35c03101576144f1bca2b3fde42222fa
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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