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Ethyl cyanoacetate → HCID 68831434, compound

HRID 2212303
Notes
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Reaction equation

HRID 2212303 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.C(O)(=O)C.C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[C:25]([C:23]#[N:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7764Ethyl cyanoacetate2×HCID 517165Ammonium AcetateHCID 21964391HCID 21964391, compound

Product 1

HCID 68831434HCID 68831434, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 241
Benzene
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzyl-3-(3-chlorophenyl)-3-methyl-4-piperidone (50 mmole), ethyl cyanoacetate (50 mmole), acetic acid (1.14 mL) ammonium acetate (400 mg), and benzene (50 mL) is heated to reflux in a Dean-Stark apparatus. After approximately 10 hours, additional ethyl cyanoacetate (50 mmole), acetic acid (1.14 mL), and ammonium acetate (400 mg) are added. After an additional 10 hours, the reaction is cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (240 mL), brine (40 mL), and dried (Na2SO4). After filtering, the extract is concentrated in vacuo and the desired product, as a mixture of E- and Z-isomers, is isolated by column chromatography on silica gel, eluting with 5% ethyl acetate/petroleum ether.

Workup

  1. temperatureis heated
  2. temperatureto reflux in a Dean-Stark apparatus
  3. waitAfter an additional 10 hours
  4. washwashed with water (240 mL), brine (40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtering
  7. concentrationthe extract is concentrated in vacuo
  8. additionthe desired product, as a mixture of E- and Z-isomers
  9. customis isolated by column chromatography on silica gel
  10. washeluting with 5% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-903f2daf61464387bc2a7c2a94a64b32
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07101905B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes