Hydrochloric Acid → 2,2,6,6-Tetramethyl-4-piperidone

HRID 1656881Notes

Reaction equation

HRID 1656881 reaction equation
[CH3:1][C:2](=[CH:4][C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[CH3:8])[CH3:3].Cl.[OH-].[NH4+:13]>>[O:10]=[C:5]1[CH2:6][C:7]([CH3:9])([CH3:8])[NH:13][C:2]([CH3:3])([CH3:1])[CH2:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10438PhoroneHCID 14923Ammonium Hydroxide

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 60%

Procedure

In a 500 mL erlenmeyer flask, 25 gm (0.182 moles) of phorone (Aldrich Chemical Company) and 250 mL of ammonium hydroxide are stirred in a water bath at 50° C. for 14 hours. Upon cooling in an ice bath, the reaction is acidified with conc. HCl and extracted (four times) with ether. The remaining water solution is first made basic with ammonium hydroxide, then saturated with NaCl and finally, extracted with ether. The ether solution is dried over anhydrous MgSO4 and evaporated to dryness, giving a pale yellow solid (I), (17 gm, 60%). A small portion of this material is recrystallized from cyclohexane, mp 34°-36° C. (lit. ref. 1) mp 35.5°-36° C.). The NMR and i.r. (1750 cm-1) confirm the presence of 4-oxo-2,2,6,6-tetramethylpiperidine.

Workup

  1. temperatureUpon cooling in an ice bath
  2. extractionextracted (four times) with ether
  3. extractionsaturated with NaCl and finally, extracted with ether
  4. dry with materialThe ether solution is dried over anhydrous MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8645bd15ea0f4a2ca36e324c34577cb5
Source dataset
uspto-grants-1993_10
Patent number
US05256397

Reaction notes

Loading…