Nitric Acid → HCID 22737748, compound

HRID 130265Notes

Reaction equation

HRID 130265 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][CH3:12].[C:14]([CH2:16][C:17]([O:19]CC)=O)#N.C(OCC)(=O)CC(C)=O.[NH:31]1CCN[CH2:33][CH2:32]1.[N+]([O-])(O)=O>CO.O.CN(C)C=O.C(O)C>[CH2:1]([C:16]1[C:17](=[O:19])[NH:31][CH:32]=[CH:33][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

10

Reactant 5

HCID 944Nitric AcidHCID 4837PiperazineHCID 7764Ethyl cyanoacetateHCID 8868Ethyl AcetoacetateHCID 13583Dodecylamine

Product 1

HCID 22737748HCID 22737748, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Into a 2 liter Erlenmeyer flask equipped with magnetic stirring was charged dodecylamine (185.0 grams, 1.0 mol; obtained from Sigma-Aldrich) followed with ethyl cyanoacetate (ECA, 135.5 grams, 1.20 mol; obtained from Sigma-Aldrich). The mixture was then heated to 140° C. and stirred at this temperature for 1 hour, during which time the ethanol by-product was allowed to distill away. Thereafter, to the hot reaction mixture stirring at 140° C. internal temperature was sequentially added dimethylformamide (DMF; 250 milliliters), ethyl acetoacetate (EAA; 266.0 grams, 2.0 mol; obtained from Sigma-Aldrich), and piperazine (PIP; 129.0 grams, 1.5 mol; obtained from Sigma-Aldrich). The mixture was then heated to 110° C. for 4 hours. The mixture was then allowed to cool to room temperature and was poured slowly into a mixture of deionized water (1,500 milliliters), methanol (3,500 milliliters), and concentrated nitric acid (270.0 grams, 3.0 mol). A white precipitate formed immediately and was allowed to stir at room temperature for 3 hours, and then was filtered and washed with a 70:30 (v/v) mixture of methanol/deionized water (500 milliliters). The precipitate was then oven dried at 60° C. to give 270.5 grams of an off white solid at 85 percent yield.

Workup

  1. customInto a 2 liter Erlenmeyer flask equipped
  2. distillationto distill away
  3. stirringThereafter, to the hot reaction mixture stirring at 140° C. internal temperature
  4. temperatureThe mixture was then heated to 110° C. for 4 hours
  5. temperatureto cool to room temperature
  6. customA white precipitate formed immediately
  7. stirringto stir at room temperature for 3 hours
  8. filtrationwas filtered
  9. washwashed with a 70:30 (v/v) mixture of methanol/deionized water (500 milliliters)
  10. customoven dried at 60° C.
  11. customto give 270.5 grams of an off white solid at 85 percent yield

Sources & evidence

ORD record
ord-bec8f6c76d3f470c865fddb4525c1259
Source dataset
uspto-grants-2008_06
Patent number
US07381253B2

Reaction notes

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