Hydrochloric Acid → HCID 86681920, compound

HRID 1749725Notes

Reaction equation

HRID 1749725 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][C:18]([O:35][CH3:36])=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[ClH:37]>C(Cl)Cl.O1CCOCC1>[ClH:37].[ClH:37].[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)=[CH:19][C:18]([O:35][CH3:36])=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681919HCID 86681919, compound

Product 1

HCID 86681920HCID 86681920, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-5-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.025 g, 0.051 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 a mixed solvent of methylene chloride and diethyl ether and thereby washed to obtain (Z)-2-[(1H-indol-3-yl)methylene]-5-methoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride (0.017 g, 73%).

Workup

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

Sources & evidence

ORD record
ord-cea83b7961574dabacc1a986a24eb461
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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