Hydrochloric Acid → HCID 22467156, compound

In 21 ml of anhydrous tetrahydrofuran were dissolved 1.50 g of 5-(4-oxocyclohexylidene)-valeric acid and 1.17 ml of triethylamine. Then, 4.50 ml of a solution of 0.80 ml of ethyl chloroformate in anhydrous tetrahydrofuran was dropwise added at −20° C., and the resulting mixture was stirred at the same temperature as above for one hour. Then, 4.50 ml of a solution of anhydrous tetrahydrofuran containing 2.00 ml of diethylamine was dropwise added at the same temperature, and the resulting mixture was stirred at ambient temperature for one hour. The reaction mixture was poured into ice water, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and saturate aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: toluene:ethyl acetate=1:1] gave 1.30 g of N,N-diethyl-5-(4-oxocyclohexylidene)-valeramide as a colorless oily product.

1. stirringthe resulting mixture was stirred at ambient temperature for one hour
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate
4. concentrationsaturate aqueous solution of sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customPurification of the residue by column chromatography [eluent: toluene:ethyl acetate=1:1]

ORD record

ord-af2e4784d9264dd2be28d36ca176b716

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384065B1