Acetic Acid → Ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate

HRID 491469Notes

Reaction equation

HRID 491469 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:22])[CH2:19][C:20]#[N:21])[CH3:16].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:15]([O:17][C:18](=[O:22])[C:19](=[C:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)[C:20]#[N:21])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 192201-Benzyl-4-piperidone

Product 1

HCID 424752Ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-benzyl-piperidin-4-one (75.1 g, 0.40 mol) in toluene (400 ml), cyano-acetic acid ethyl ester (50.6 ml, 0.48 mol) and acetic acid (18.2 ml, 0.32 mol) are added at ambient temperature. The reaction mixture is refluxed for 4 h, quenched with ice-water and extracted with diethyl ether. The combined extracts are washed with H2O, brine and dried over sodium sulphate to give (1-benzyl-piperidin-4-ylidene)-cyano-acetic acid ethyl ester in quantitative yield.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 h
  2. customquenched with ice-water
  3. extractionextracted with diethyl ether
  4. washThe combined extracts are washed with H2O, brine
  5. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-27295c9f17334de7ae2894bc6a6df5b1
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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