Methanol → N-cyclohexyl-3,3-dimethoxy-butyramide

HRID 426543

Reaction equation

HRID 426543 reaction equation
[CH:1]1([NH:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:14]([O-])([O-])[O:15]C.[CH3:19]O>C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C2C(=CC=CC=2)C=CC=1>[CH:1]1([NH:7][C:8](=[O:13])[CH2:9][C:10]([O:15][CH3:14])([O:12][CH3:19])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 70805N-CyclohexylacetoacetamideHCID 53629101Methylorthoformate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 7047QuinolineCatalyst

Conditions

Temperature
25 °C

Procedure

A mixture of 36.6 g of N-cyclohexyl-acetylacetamide, 32 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was stirred for 4 hours at 25° C. and after the addition of 2 g of quinoline, the mixture was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was cooled and vacuum filtered. The recovered precipitate was dried to obtain 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide melting at 66° C.

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. additionThe residue was added to isopropyl ether
  3. temperaturethe mixture was cooled
  4. filtrationvacuum filtered
  5. customThe recovered precipitate was dried

Sources & evidence

ORD record
ord-0129d5d8f9f04f7ba04bc9fb4c31988a
Source dataset
uspto-grants-1979_10
Patent number
US04170465

Linked notes

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