Hydrochloric Acid → HCID 86681915, compound

HRID 1749717Notes

Reaction equation

HRID 1749717 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]([OH:35])[C:18]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[ClH:42]>C(Cl)Cl.O1CCOCC1>[ClH:42].[ClH:42].[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][NH:25][CH2:24][CH2:23]4)=[C:19]([OH:35])[C:18]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681914HCID 86681914, compound

Product 1

HCID 86681915HCID 86681915, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-5-phenyl-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.031 g, 0.056 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 mixture was azeotroped twice with toluene under reduced pressure, and then the residual solid was suspended in methylene chloride and thereby washed to obtain (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-5-phenyl-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride (0.023 g, 78%).

Workup

  1. customThe mixture was azeotroped twice with toluene under reduced pressure
  2. washwashed

Sources & evidence

ORD record
ord-8dc2d2850040451cbbdcaba28ab12857
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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