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

HRID 1468558Notes

Reaction equation

HRID 1468558 reaction equation
C(CC([O-])=O)#N.[CH2:7]([N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:22].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17](=[C:23]([C:21]#[N:22])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 192201-Benzyl-4-piperidoneHCID 1551036Cyanoacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

[A] Synthesis of 1-benzyl-piperidin-4-ylidene)-cyanoacetate (2; FIG. 4). A solution of 1-benzyl-piperidin-4-one (75.1 g, 0.40 mol) in toluene (9400 mL), ethyl cyanoacetate (50.6 mL, 0.48 mol) and acetic acid (918.2 mL, 0.32 mol) was refluxed for 4 hr. The mixture was quenched with ice-water and extracted with diethyl ether. The combined extracts were washed with water, brine and dried over Na2SO4 to give ethyl (1-benzyl-piperidin-4-ylidene)cyanoacetate in quantitative yield. Rf=0.53 (hexane:AcOEt=1:1).

Workup

  1. customThe mixture was quenched with ice-water
  2. extractionextracted with diethyl ether
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e922ed0ddac0459fa0e723f698b91835
Source dataset
uspto-grants-2015_04
Patent number
US09005578B2

Reaction notes

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