Hydrochloric Acid → Stearyl Pyridone

HRID 2355667

Reaction equation

HRID 2355667 reaction equation
[CH2:1](N)[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(OCC)(=O)CC(C)=O.[NH:37]1CCC[CH2:39][CH2:38]1.Cl>CO.CN(C)C=O>[CH2:1]([C:22]1[C:23](=[O:25])[NH:37][CH:38]=[CH:39][CH:20]=1)[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]

Participants

8

Reactant 5

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

Product 1

HCID 86605271Stearyl PyridoneYield 65.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Into a 2 liter Erlenmeyer flask equipped with magnetic stirring was charged stearylamine (118 g, 0.44 mol; obtained from Sigma-Aldrich) and ethyl cyanoacetate (ECA, 45.2 grams, 0.4 mol). The mixture was heated to 120° C. for 90 minutes, after which ethyl acetoacetate (EAA, 114 grams, 0.88 mol), piperidine (PIP; 70 grams, 0.82 mol), and dimethylformamide (DMF; 140 milliliters) were added. The mixture was heated to 120° C. for 4 hours. The mixture was then allowed to cool to room temperature and was poured slowly into well stirred methanol (1,200 milliliters), which contained concentrated hydrochloric acid (100 milliliters). The resulting suspension was allowed to stir for 10 minutes, and was then filtered and washed with 3×200 milliliter portions of methanol. The resulting solid was oven dried at 60° C. to give 91.3 grams of a beige powder at 57 percent yield.

Workup

  1. customInto a 2 liter Erlenmeyer flask equipped
  2. temperatureThe mixture was heated to 120° C. for 4 hours
  3. temperatureto cool to room temperature
  4. stirringto stir for 10 minutes
  5. filtrationwas then filtered
  6. washwashed with 3×200 milliliter portions of methanol
  7. customdried at 60° C.

Sources & evidence

ORD record
ord-76cb7fd8c69843af9908c5081454fcea
Source dataset
uspto-grants-2010_07
Patent number
US07754862B2

Linked notes

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