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

HRID 1030030Notes

Reaction equation

HRID 1030030 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]>>[CH3:8][C:7]1([CH3:9])[CH2:6][C:5](=[O:10])[CH2:4][C:2]([CH3:3])([CH3:1])[NH:13]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10438PhoroneHCID 14923Ammonium Hydroxide

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 78%

Procedure

This compound was prepared according to the method of Sandris and Ourisson, Bull. Soc. Chim. Fr. 25: 345 (1958), in which 25 gms (180 mmoles) of phorone and 180 mls of ammonium hydroxide are stirred at 35° C. for 12 hrs. The solution is then cooled in an ice bath and concentrated HCl is added until the pH of the solution is 1. This solution is then saturated with NaCl and extracted with ether. The pH of the remaining liquid is raised to 10 with ammonium hydroxide followed by ether extraction. The ether solution is then dried with anhydrous sodium sulfate and evaporated to dryness, in vacuo, giving 20 gms (78%) of the desired product, B. P. 80°-85° C. at 15 mm Hg.

Workup

  1. customThis compound was prepared
  2. temperatureThe solution is then cooled in an ice bath
  3. extractionsaturated with NaCl and extracted with ether
  4. temperatureThe pH of the remaining liquid is raised to 10 with ammonium hydroxide
  5. extractionfollowed by ether extraction
  6. dry with materialThe ether solution is then dried with anhydrous sodium sulfate
  7. customevaporated to dryness, in vacuo

Sources & evidence

ORD record
ord-2d2bc7dd797c42499df4886619a95811
Source dataset
uspto-grants-1992_04
Patent number
US05104641

Reaction notes

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