Hydrochloric Acid → HCID 71278551, compound

HRID 1749761Notes

Reaction equation

HRID 1749761 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([OH:35])=[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:13]=3[O:12]2)=[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]([CH2:10][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]([OH:35])[CH:18]=[CH:17][C:14]=3[C:15]=2[OH:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71278747HCID 71278747, compound

Product 1

HCID 71278551HCID 71278551, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-({2-[(1H-indol-3-yl)methyl]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.020 g, 0.042 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was added with triethylamine and thereby made basic. Then, the mixture was azeotroped twice with toluene under reduced pressure, and the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain 2-[(1H-indol-3-yl)methyl]-7-(piperazin-1-ylmethyl)benzofuran-3,6-diol (0.011 g, 69%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with triethylamine
  3. customThen, the mixture was azeotroped twice with toluene under reduced pressure
  4. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-59103f095c5b40f2bc0817f5302fc0eb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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