Pyridine → HCID 23128496, compound

HRID 1468258Notes

Reaction equation

HRID 1468258 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl.[CH3:19][NH:20][O:21][CH3:22]>ClCCl>[CH:1]1([CH2:7][CH2:8][C:9]([N:20]([O:21][CH3:22])[CH3:19])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2734098Cyclohexylpropionyl chloride

Product 1

HCID 23128496HCID 23128496, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyclohexylpropionic chloride (1.00 g, 5.71 mmol) was dissolved in dichloromethane (10 mL). Under ice-cooled condition, pyridine (0.910 mL, 11.3 mmol) and N,O-dimethylhydroxylamine hydrochloride (840 mg, 8.57 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 3-cyclohexyl-N-methoxy-N-methylpropaneamide (1.13 g, yield 99%).

Workup

  1. additionwere added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. additionafter adding a saturated sodium hydrogen carbonate aqueous solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)

Sources & evidence

ORD record
ord-71bc5638354e463fa578e4daea98edc9
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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