Ethyl cyanoacetate → HCID 58922466, compound

HRID 639157Notes

Reaction equation

HRID 639157 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8]/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.[CH:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)=O.[C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[N:28].N1CCCCC1>C(O)C>[NH2:28][C:27]1[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:9]([CH3:16])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 14691153HCID 14691153, compound

Product 1

HCID 58922466HCID 58922466, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 100 mg (0.46 mmol) ethyl(2E)-3-[(3-methylphenyl)amino]-2-butenoate (preparation analogously to Example 1A), 59.80 mg (0.46 mmol) 4-formylbenzonitrile and 51.58 mg (0.46 mmol) ethyl cyanoacetate are dissolved in 2 ml ethanol. 77.66 mg (90 μl, 0.91 mmol) piperidine are added to the mixture which is stirred at reflux overnight. After the reaction is finished, the mixture is purified by preparative HPLC followed by column chromatography on silica with dichloromethane as eluent.

Workup

  1. temperatureat reflux overnight
  2. customthe mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-90deba1de5a148feae6a25f06e725306
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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