Cyclohexanecarbonyl chloride → N-[(2,2-Dimethoxy)ethyl]-N-(2-pyridyl)cyclohexanecarboxamide

HRID 1603681Notes

Reaction equation

HRID 1603681 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.C([Li])CCC.[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:25]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:26]

Participants

5

Reactant 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 217139332-(2,2-Dimethoxyethylamino)pyridineHCID 178418339Butyllithium

Product 1

HCID 21713913N-[(2,2-Dimethoxy)ethyl]-N-(2-pyridyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6 g of 2-[(2-pyridyl)amino]acetaldehyde dimethyl acetal (prepared as described in Beilstein E III/IV, 22, 3871) in 40 ml of tetrahydrofuran stirred at 0° C. was added dropwise 13.2 ml of butyl lithium (2.5 M solution in n-hexane) and the resulting mixture was stirred at room temperature for 1 h. Afterwards, to the solution was added dropwise in 5 min 4.46 ml of cyclohexanecarbonyl chloride. Stirring was continued for 5.5h, followed by in vacuo evaporation of the reaction mixture to dryness. The residue was purified by flash chromatography (chloroform-ethyl acetate 7:3) affording 13.3 g of the title compound.

Workup

  1. stirringStirring
  2. customfollowed by in vacuo evaporation of the reaction mixture to dryness
  3. customThe residue was purified by flash chromatography (chloroform-ethyl acetate 7:3)

Sources & evidence

ORD record
ord-62b3fa744e954d2e9ce7b95b334f512f
Source dataset
uspto-grants-1999_11
Patent number
US05990114

Reaction notes

Loading…