Ethanol → HCID 59651903, compound

HRID 887020Notes

Reaction equation

HRID 887020 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]C(=O)C)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:26]([OH:30])(=O)[CH:27]=O.O.[NH2:32][NH2:33].[CH3:34][CH2:35]O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:35]([CH3:34])=[N:32][NH:33][C:26](=[O:30])[CH:27]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrateHCID 59651914HCID 59651914, compound

Product 1

HCID 59651903HCID 59651903, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[4-(2-oxo-propyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (7.01 g, 21.03 mmol) and glyoxalic acid hydrate (1.9 g, 21 mmol) was heated to 100° C. for 5 h. The resulting dark thick oil was stirred in 30 mL of EtOH as hydrazine hydrate (2.1 g, 42 mmol) was added. After stirred at 90° C. for 5 hr, the reaction was cooled to rt, and the solvent was evaporated. The crude product was purified by flash chromatography (10% MeOH in CH2Cl2), followed by trituration with ether to give 4-[4-(3-methyl-6-oxo-1,6-dihydro-pyridazin-4-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (3.25 g, 46%): Mp 184-6° C.; MS m/z 386 (M+H).

Workup

  1. additionwas added
  2. temperaturethe reaction was cooled to rt
  3. customthe solvent was evaporated
  4. customThe crude product was purified by flash chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0fc7c53ea6e548aa9597a3c97e9e6a5a
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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