N-cyclohexyl-3,3-dimethoxy-butyramide → N-cyclohexyl-3-methoxy-crotonamide

HRID 426544Notes

Reaction equation

HRID 426544 reaction equation
[CH:1]1([NH:7][C:8](=[O:16])[CH2:9][C:10](OC)([O:12][CH3:13])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1>[CH:1]1([NH:7][C:8](=[O:16])/[CH:9]=[C:10](\[O:12][CH3:13])/[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 20390362N-cyclohexyl-3,3-dimethoxy-butyramide

Product 1

HCID 70612346N-cyclohexyl-3-methoxy-crotonamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide in 200 ml of toluene was stirred and heated to 145° C. to distill an azeotrope of toluene and methanol. After 3 hours, the mixture was cooled and evaporated to dryness under reduced pressure. The oil residue was chromatographed over silica gel and was eluted with a 7-3 methylene chlorideethyl acetate mixture. The fractions with an Rf of 0.55 were recovered and were concentrated to dryness under reduced pressure. The residue was added to isopropyl ether which was iced and vacuum filtered. The recovered precipitate was dried to obtain 18 g of N-cyclohexyl-3-methoxy-crotonamide melting at 109° C.

Workup

  1. distillationto distill an azeotrope of toluene and methanol
  2. temperaturethe mixture was cooled
  3. customevaporated to dryness under reduced pressure
  4. customThe oil residue was chromatographed over silica gel
  5. washwas eluted with a 7-3 methylene chlorideethyl acetate mixture
  6. customThe fractions with an Rf of 0.55 were recovered
  7. concentrationwere concentrated to dryness under reduced pressure
  8. additionThe residue was added to isopropyl ether which
  9. filtrationvacuum filtered
  10. customThe recovered precipitate was dried

Sources & evidence

ORD record
ord-e993e3dc7ca84fef813719eb150caf42
Source dataset
uspto-grants-1979_10
Patent number
US04170465

Reaction notes

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