Hydrochloric Acid → N-Formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide

HRID 1603682Notes

Reaction equation

C[O:2][CH:3](OC)[CH2:4][N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH:3]([CH2:4][N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.46 g of N-[(2,2-dimethoxy)ethyl]-N-(2-pyridyl)cyclohexanecarboxamide, 0.05 g of 1,4-hydroquinone, and 25 ml of 2N HCl was stirred at 80° C. for 20 min under nitrogen stream. Afterwards, it was cooled at 0° C., diluted with 50 ml of methylene chloride, and alkalinized to pH=10 with 20% aqueous Na2CO3. The aqueous layer was extracted twice with methylene chloride and the combined organic layers were dried (sodium sulfate) and evaporated to dryness in vacuo affording 0.94 g of the title compound, used without further purification in the next reaction step.

Workup

temperatureAfterwards, it was cooled at 0° C.
extractionThe aqueous layer was extracted twice with methylene chloride
dry with materialthe combined organic layers were dried (sodium sulfate)
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-84bf3953783a447cad373a8c0efc8f7c
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990114

Reaction notes

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