Methanesulfonic Acid → HCID 22485480, compound

HRID 2181324Notes

Reaction equation

HRID 2181324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:26]=[CH:27][C:28]([C:31]5[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=5)=[N:29][CH:30]=4)[CH2:21][CH2:20]3)=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>CO.C(Cl)Cl>[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:38][O:37][C:35]1[CH:36]=[C:31]([C:28]2[CH:27]=[CH:26][C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:16]4[CH:17]=[CH:18][C:13]([C:5]5[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=5)=[N:14][CH:15]=4)[CH2:24][CH2:23]3)=[CH:30][N:29]=2)[CH:32]=[C:33]([O:41][CH3:42])[C:34]=1[O:39][CH3:40]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485481HCID 22485481, compound

Product 1

HCID 22485480HCID 22485480, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 1,4-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]piperazine (143.0 mg, 0.250 mmol) in methanol-methylene chloride (1:2, 6.0 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.50 mL, 0.50 mmol), and the reaction mixture was concentrated under reduced pressure. Ethanol (5.0 mL) was added to the residue, and the mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-chloroform-diethyl ether to yield the title compound as yellow needles [melting point: 262.0° C. (decomposed)](171.0 mg, yield: 89%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthanol (5.0 mL) was added to the residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was recrystallized from methanol-chloroform-diethyl ether

Sources & evidence

ORD record
ord-f59bcf0d22a44f66b0f11f8af9aba098
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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