Triethylamine → 1-Acryloyl-2,6-diethyl-2,3,6-trimethylpiperidine

HRID 66252Notes

Reaction equation

HRID 66252 reaction equation
[CH2:1]([C:3]1([CH3:13])[CH:8]([CH3:9])[CH2:7][CH2:6][C:5]([CH2:11][CH3:12])([CH3:10])[NH:4]1)[CH3:2].[C:14](Cl)(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:14]([N:4]1[C:5]([CH2:11][CH3:12])([CH3:10])[CH2:6][CH2:7][CH:8]([CH3:9])[C:3]1([CH2:1][CH3:2])[CH3:13])(=[O:17])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 205360782,6-Diethyl-2,3,6-trimethylpiperidine

Product 1

HCID 227545731-Acryloyl-2,6-diethyl-2,3,6-trimethylpiperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

36.7 g of 2,6-diethyl-2,3,6-trimethylpiperidine (Compound No. 1) are dissolved in 200 ml toluene. A solution of 19 g acrylic chloride in 50 ml toluene is added slowly within an hour and the mixture is stirred at 70°-75° C. for 18 hours. After addition of 21.2 g of triethylamine the stirring is continued for another 24 hours. After cooling the reaction mixture is washed twice with 100 ml water each. The toluene solution is dried over sodium sulfate and evaporated. The residue is distilled in vacuo and there is obtained the 1-acryloyl-2,6-diethyl-2,3,6-trimethylpiperidine (Compound No. 12) as distillate at 133°-135° C./0.6 mm Hg.

Workup

  1. waitis continued for another 24 hours
  2. temperatureAfter cooling the reaction mixture
  3. washis washed twice with 100 ml water each
  4. dry with materialThe toluene solution is dried over sodium sulfate
  5. customevaporated
  6. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-eb10d7c1a1e14f47b5cccd80dd7a2c25
Source dataset
uspto-grants-1978_12
Patent number
US04131599

Reaction notes

Loading…