1,4-Dioxane hydrochloride → 4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl hydrazinecarboxylate trihydrochloride

HRID 1465475Notes

Reaction equation

HRID 1465475 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34](=[O:36])[CH3:35])[CH2:30][CH2:29]3)=[CH:24][N:23]=2)=[CH:16][CH:15]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:43]>ClCCl>[ClH:43].[ClH:43].[ClH:43].[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34](=[O:36])[CH3:35])[CH2:30][CH2:29]3)=[CH:24][N:23]=2)=[CH:16][CH:15]=1)=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 581813324-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 670298164-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl hydrazinecarboxylate trihydrochlorideYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl tert-butyl hydrazine-1,2-dicarboxylate (139.2 mg, 0.2797 mmol) in anhydrous dichloromethane (1.4 ml) was added 4M hydrogen chloride dioxane solution (1.4 ml, 5.6 mmol). After stirring at room temperature for 8 hrs, the mixture was concentrated under reduced pressure. Ethyl acetate was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. The operation was repeated twice to azeotropically remove hydrogen chloride gas. The residue was dissolved in ethanol (6 ml), and ethyl acetate (30 ml) was added. The precipitated solid was filtered and dried under reduced pressure to give the title compound (105.3 mg, yield 74.3%) as a slightly yellow solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the concentrated residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. dissolutionThe residue was dissolved in ethanol (6 ml)
  5. additionethyl acetate (30 ml) was added
  6. filtrationThe precipitated solid was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-90793235085f4258a6184f471a2769d4
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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