Hydrochloric Acid → N-stearyl pyridone

HRID 1369129

Reaktionsgleichung

Reaktionsgleichung von HRID 1369129
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([CH2:22][C:23]([O:25]CC)=O)#N.[C:28](OCC)(=O)[CH2:29]C(C)=O.N1CCCCC1.Cl>O.CO.COCCOC.C1(C)C=CC=CC=1>[CH2:1]([N:19]1[CH:29]=[CH:28][CH:20]=[CH:22][C:23]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 15793Octadecylamine

Produkt 1

HCID 21388044N-stearyl pyridoneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Into a 2 liter Erlenmeyer flask equipped with magnetic stir bar and temperature thermostat was charged octadecylamine (stearylamine, 18.9 grams, 0.07 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.) followed with ethyl cyanoacetate (7.9 grams, 0.07 mol, density 1.06 grams per milliliter; obtained from Spectrum Chemicals, New Brunswick, N.J.). The resulting colorless mixture was stirred and heated to 120° C. internal temperature for 1 hour, during which time a byproduct was distilled away. To the hot reaction mixture was then sequentially added ethyl acetoacetate (10.08 grams, 0.0775 mol, density 1.02 grams per milliliter, obtained from Lonza Group, Germany), piperidine (11.0 grams, 0.13 mol, density 0.861 grams per milliliter; obtained from Sigma-Aldrich Co.), and a solvent mixture (60 milliliters) containing 5 parts by weight toluene and 1 part by weight 1,2-dimethoxyethane. The reaction proceeded with stirring at 120° C. for another 24 hours. The solvents were then distilled off in vacuo, and the remaining viscous brown solution was carefully poured into a stirring solution of methanol (80 milliliters), deionized water (20 milliliters), and concentrated hydrochloric acid (16 milliliters, 2.5 mol). A solid tan precipitate formed instantly and the slurry was vacuum filtered followed by rinsing the solid cake with 2×50 milliliter portions of 80 percent aqueous methanol. The cake thus obtained was air-dried for 24 hours to afford 24.5 grams (0.061 mol, 87 percent yield) of N-stearyl pyridone product as light tan powder.

Aufarbeitung

  1. customInto a 2 liter Erlenmeyer flask equipped with magnetic stir bar
  2. distillationduring which time a byproduct was distilled away
  3. stirringwith stirring at 120° C. for another 24 hours
  4. distillationThe solvents were then distilled off in vacuo
  5. customA solid tan precipitate formed instantly
  6. filtrationfiltered
  7. washby rinsing the solid cake with 2×50 milliliter portions of 80 percent aqueous methanol
  8. customThe cake thus obtained
  9. customwas air-dried for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-4865b638a9e04faeb68bfb49e31c1ebd
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06576747B1

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