Dimethyl malonate → HCID 22341500, compound

HRID 584914Notes

Reaction equation

HRID 584914 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:25])[C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)=[CH:5][CH:4]=1)=O.[C:26]([O:33][CH3:34])(=[O:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:25][N:16]([CH2:15][C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[C:27]([C:26]([O:33][CH3:34])=[O:32])[C:28]([O:30][CH3:31])=[O:29])=[CH:8][CH:7]=2)[CH:14]=[CH:13][CH:12]=1)[C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:24]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 9793820Piperidine, acetateHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

Product 1

HCID 22341500HCID 22341500, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.4 g (4.25 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared as in Example 1(e)), 20 ml of toluene, 560 mg (4.25 mmol) of dimethyl malonate and 125 mg (0.85 mmol) of piperidine acetate are introduced into a three-necked flask under a stream of nitrogen. The mixture is refluxed for 6 hours, while separating out the water formed using Dean-Stark apparatus. The reaction medium is cooled, extracted with ethyl acetate and washed with water. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The crude product is purified by chromatography on a column of silica eluted with admixture of heptane and ethyl acetate (70/30). After evaporation of the solvents, 1.4 g (75%) of the expected product are collected.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customwhile separating out the water
  3. customformed
  4. temperatureThe reaction medium is cooled
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. customThe organic phase is separated out
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe crude product is purified by chromatography on a column of silica
  11. washeluted with admixture of heptane and ethyl acetate (70/30)
  12. customAfter evaporation of the solvents, 1.4 g (75%) of the expected product
  13. customare collected

Sources & evidence

ORD record
ord-fdd286fff02845ff88a26f3b89294ffa
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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