Ethyl cyanoacetate → Ethyl cyano(2,2,6,6-tetramethylpiperidin-4-ylidene)acetate

HRID 903401

Reaction equation

HRID 903401 reaction equation
[CH3:1][C:2]1([CH3:11])[NH:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:4](=O)[CH2:3]1.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C([O-])(=O)C.[NH4+].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[CH2:3][C:4](=[C:14]([C:12]#[N:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][C:7]([CH3:10])([CH3:9])[NH:8]1

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 517165Ammonium Acetate

Product 1

HCID 712423Ethyl cyano(2,2,6,6-tetramethylpiperidin-4-ylidene)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

155 g (1 mol) of triacetonamine, 113 g of ethyl cyanoacetate, 300 ml of benzene and 31 g of ammonium acetate are kept under reflux for 1.5 hours under a water separator. The benzene phase is treated with 50% of potassium carbonate, the organic phase is dried over sodium sulphate and the benzene is then stripped off in vacuo. Ethyl 2,2,6,6-tetramethyl-4-piperidinylidene-cyanoacetate is obtained as an oily residue.

Workup

  1. temperatureunder reflux for 1.5 hours under a water separator
  2. dry with materialthe organic phase is dried over sodium sulphate

Sources & evidence

ORD record
ord-583f1886561042f2826db9926c648525
Source dataset
uspto-grants-1980_10
Patent number
US04226999

Linked notes

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