1,4-Dioxane hydrochloride → (4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-piperazin-1-yl-methanone

HRID 1173870Notes

Reaction equation

HRID 1173870 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:29][C:30]3[NH:31][CH:32]=[CH:33][N:34]=3)[CH2:23][C:24]3[NH:25][CH:26]=[CH:27][N:28]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH:25]1[CH:26]=[CH:27][N:28]=[C:24]1[CH2:23][N:22]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:35])=[CH:20][CH:19]=1)[CH2:29][C:30]1[NH:34][CH:33]=[CH:32][N:31]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66941477HCID 66941477, compound

Product 1

HCID 21084462(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-piperazin-1-yl-methanoneYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (111 mg) obtained in Example 32-1 was dissolved in anhydrous methanol (1.0 ml) and then added with a 4 mol/l hydrogen chloride/dioxane solution (3.0 ml) and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off and the residue was added with a 1 mol/l sodium hydroxide aqueous solution, followed by washing with dichloromethane. The aqueous layer was evaporated to dryness, followed by distilling azeotropically with chloroform. Consequently, the subject compound (48.5 mg) was obtained as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was added with a 1 mol/l sodium hydroxide aqueous solution
  4. washby washing with dichloromethane
  5. customThe aqueous layer was evaporated to dryness
  6. distillationby distilling azeotropically with chloroform

Sources & evidence

ORD record
ord-6afa5487e2394cbbb85f8fe887f6840f
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…