Acetic Anhydride → 1-(3-Hydroxypiperidin-1-yl)ethan-1-one

HRID 1390494Notes

Reaction equation

HRID 1390494 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 232933-Hydroxypiperidine

Product 1

HCID 218970301-(3-Hydroxypiperidin-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

3-Hydroxypiperidine (0.4 mole) is dissolved in 150 ml. of methylene chloride. The solution is cooled to 10° C. and acetic anhydride (0.46 mole) is added dropwise, maintaining the temperature under 20° C. The reaction mixture is allowed to come to room temperature, and is then refluxed for 2 hours. The methylene chloride is evaporated off, and the remaining liquid is distilled under high vacuum. A thick yellow oil is collected at 122°-126° C. (0.3 mm Hg).

Workup

  1. temperaturemaintaining the temperature under 20° C
  2. customto come to room temperature
  3. temperatureis then refluxed for 2 hours
  4. customThe methylene chloride is evaporated off
  5. distillationthe remaining liquid is distilled under high vacuum
  6. customA thick yellow oil is collected at 122°-126° C. (0.3 mm Hg)

Sources & evidence

ORD record
ord-2dc67882acb245708917af752d75762d
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

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