Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1) → HCID 21098365, compound

HRID 713410

Reaction equation

HRID 713410 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(O[C:22](=N)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 21098365HCID 21098365, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.15 g, 4.73 mmol, 1.0 eq) in EtOH (15 mL) was added benzimidic acid ethyl ester hydrochloride (921 mg, 4.96 mmol, 1.05 eq.) and the reaction mixture was refluxed for 48 h. The inorganic precipitate was filtered off, washed with ethyl acetate, and the solvent of the mother liquor was evaporated in vacuo. The residue was purified by column chromatography (ethyl acetate/heptanes) to give the title compound as a white solid (327 mg, 0.99 mmol). MS (m/z, MH+): 330.2

Workup

  1. temperaturethe reaction mixture was refluxed for 48 h
  2. filtrationThe inorganic precipitate was filtered off
  3. washwashed with ethyl acetate
  4. customthe solvent of the mother liquor was evaporated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-fef1ec9c13244d4393c3ab5c1ec1c115
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Linked notes

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