1,4-Dioxane hydrochloride → 6-(Piperazin-1-ylsulfonyl)isoquinoline dihydrochloride

HRID 1845952Notes

Reaction equation

HRID 1845952 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[N:22][CH:21]=[CH:20]3)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:27].O1CCOCC1>ClCCl>[ClH:27].[ClH:27].[N:11]1([S:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[N:22][CH:21]=[CH:20]3)(=[O:16])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 667272096-(4-Tert-butoxycarbonylpiperazin-1-ylsulfonyl)isoquinoline

Product 1

HCID 667271316-(Piperazin-1-ylsulfonyl)isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg of 6-(4-tert-butoxycarbonylpiperazin-1-ylsulfonyl)isoquinoline was dissolved in 10 mL of dichloromethane, and 1 mL of 4 M hydrochloric acid-dioxane solution was added dropwise thereto with stirring and then reacted at room temperature for 3 hours. From the reaction solution, the solvent was distilled off, and the obtained residue was dissolved in 0.5 mL of methanol. Then, 5 mL of ethyl acetate was added with vigorous stirring, and the deposited white crystal was collected by filtration and dried to obtain 35 mg of the compound of interest as a white crystal (25%).

Workup

  1. customreacted at room temperature for 3 hours
  2. distillationFrom the reaction solution, the solvent was distilled off
  3. dissolutionthe obtained residue was dissolved in 0.5 mL of methanol
  4. additionThen, 5 mL of ethyl acetate was added with vigorous stirring
  5. filtrationthe deposited white crystal was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-905fa7bd360a427aba8ee9e6cb99a745
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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