Hydrochloric Acid → HCID 86681960, compound

HRID 1749764Notes

Reaction equation

HRID 1749764 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/[C:12](=[O:35])[C:13]3[C:18]([CH2:19]/2)=[C:17]([CH2:20][N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[C:16]([OH:34])=[CH:15][CH:14]=3)=[CH:2]1.[ClH:36]>C(Cl)Cl.O1CCOCC1>[ClH:36].[ClH:36].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2/[C:12](=[O:35])[C:13]3[C:18]([CH2:19]/2)=[C:17]([CH2:20][N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[C:16]([OH:34])=[CH:15][CH:14]=3)=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681959HCID 86681959, compound

Product 1

HCID 86681960HCID 86681960, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (E)-4-({2-[(1H-indol-3-yl)methylene]-5-hydroxy-1-oxo-2,3-dihydro-1H-inden-4-yl}methyl)piperazine-1-carboxylate (0.030 g, 0.063 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 1 hour. The mixture was azeotroped twice with toluene under reduced pressure, and the residual solid was suspended in methylene chloride and thereby washed to obtain (E)-2-[(1H-indol-3-yl)-methylene]-5-hydroxy-4-(piperazin-1-ylmethyl)-2,3-dihydro-1H-inden-1-one dihydrochloride (0.024 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-808558983b9c41c18cc3a65c0ecfc7cc
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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