1,4-Dioxane hydrochloride → N-{4-[2-(4-hydrazinocarbonylmethylphenyl)ethyl]phenyl}acetamide hydrochloride

HRID 1465434Notes

Reaction equation

HRID 1465434 reaction equation
O1CCOCC1.[ClH:7].[C:8]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][NH:30]C(OC(C)(C)C)=O)=[O:28])=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)(=[O:10])[CH3:9]>>[ClH:7].[NH:29]([C:27]([CH2:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[CH:17][CH:16]=2)=[CH:25][CH:24]=1)=[O:28])[NH2:30]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67030250Tert-butyl 2-({4-[(4-acetamidophenyl)ethyl]phenyl}acetyl)hydrazinecarboxylate

Product 1

HCID 67030104N-{4-[2-(4-hydrazinocarbonylmethylphenyl)ethyl]phenyl}acetamide hydrochlorideYield 98%

Procedure

4M-Hydrogen chloride dioxane solution (1 ml, 4 mmol) was added to tert-butyl 2-({4-[(4-acetamidophenyl)ethyl]phenyl}acetyl)hydrazinecarboxylate (23 mg, 0.056 mmol), and the mixture was stirred at room temperature for 15 mins. The reaction mixture was concentrated under reduced pressure, dichloromethane was added, and the mixture was concentrated again, and hydrogen chloride gas was removed. The precipitate was collected by filtration, washed with diethyl ether and dried under reduced pressure to give the title compound (18 mg, yield 98%) as a slightly yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, dichloromethane
  2. additionwas added
  3. concentrationthe mixture was concentrated again
  4. customhydrogen chloride gas was removed
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cab499f9c9944612ae025fd8380c79e1
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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