Acetic Acid → HCID 11073421, compound

HRID 1167253Notes

Reaction equation

HRID 1167253 reaction equation
C([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=CCC.C(#N)[CH:12]=[CH2:13].C(O)(=[O:17])C.O>C(#N)C>[CH2:12]([CH:7]([CH:6]=[O:17])[CH2:8][CH2:9][C:10]#[N:5])[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7855AcrylonitrileHCID 138955HCID 138955, compound

Product 1

HCID 11073421HCID 11073421, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of N-(1-buten-1-yl)piperidine [Mannich, D.; Ber. 1936, 69, 2106] (4.2 g, 29.9 mmol) and acrylonitrile (2.1 g, 38.8 mmol) in acetonitrile (25 mL) was heated at reflux for 18 hours. Acetic acid and water (10 mL, 1:1) was added and the reaction was heated an additional 4 hours. The acetonitrile was removed in vacuo and the residue was taken up in ether (60 mL). The ether was washed with water (2×40 mL), saturated sodium bicarbonate/water (40 mL), dried (magnesium sulfate), concentrated in vacuo and then distilled to afford the title compound (1.6 g, 42%) as a colorless liquid. bp 132° C. (18 mm);

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturethe reaction was heated an additional 4 hours
  3. customThe acetonitrile was removed in vacuo
  4. washThe ether was washed with water (2×40 mL), saturated sodium bicarbonate/water (40 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. distillationdistilled

Sources & evidence

ORD record
ord-99a0fe06859c40abbf317fe816ff398a
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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