Acetic Anhydride → 1-Acetyl-2-piperidinecarbonitrile

HRID 1077083Notes

Reaction equation

HRID 1077083 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([NH2:5])=O.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:10]([N:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]#[N:5])(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 140623Piperidine-2-carboxamide

Product 1

HCID 126800871-Acetyl-2-piperidinecarbonitrileYield 67%

Procedure

An amount of 19.2 g. (0.15 moles) of pipecolamide is added portionwise to 102 g. (1.0 moles) of acetic anhydride over a 15 minute period with stirring. The temperature rises to ca. 60°C. The mixture is then heated to reflux, during which the solid dissolves and the solution turns a dark brown. After refluxing for 4 hours, the reaction mixture is subjected to vacuum distillation (first at 60 mm Hg to remove acetic acid and excess acetic anhydride, and then at 1-4 mm Hg pressure). Thus is obtained 15.3 grams of 1-acetyl-2-cyanopiperidine, boiling at 104°-14°C. This corresponds to a 67% yield based on pipecolamide.

Workup

  1. customrises to ca. 60°C
  2. temperatureThe mixture is then heated
  3. temperatureto reflux, during which the solid
  4. dissolutiondissolves
  5. temperatureAfter refluxing for 4 hours
  6. distillationthe reaction mixture is subjected to vacuum distillation (first at 60 mm Hg
  7. customto remove acetic acid and excess acetic anhydride

Sources & evidence

ORD record
ord-c2b04d1519324abd93cef76125d2579c
Source dataset
uspto-grants-1976_05
Patent number
US03959365

Reaction notes

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