Triethylamine → 1-[5-(3,4,5-Trimethoxyphenyl)-2,4-pentadienoyl]-4-(methylaminocarbonylmethyl)-piperazine

HRID 542179

Reaction equation

HRID 542179 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=[CH:16][C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[CH3:32][NH:33][C:34](=[O:37])[CH2:35]Cl>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=[CH:16][C:17]([N:19]2[CH2:20][CH2:21][N:22]([CH2:35][C:34]([NH:33][CH3:32])=[O:37])[CH2:23][CH2:24]2)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 667732-chloro-N-methylacetamideHCID 539540541-[5-(3,4,5-Trimethoxyphenyl)-2,4-pentadienoyl]-piperazine

Product 1

HCID 544790041-[5-(3,4,5-Trimethoxyphenyl)-2,4-pentadienoyl]-4-(methylaminocarbonylmethyl)-piperazineYield 71.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22987606Toluene trichloromethaneSolvent

Procedure

To a solution of 302 mg of 1-[5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl]-piperazine in dry toluene (12 ml) were added in an atmosphere of argon 1.3 ml of triethylamine and subsequently a solution of 254 mg of N-methylchloroacetamide in dry toluene-chloroform (1:1, 2 ml). The mixture was refluxed for 8 hours. To the reaction mixture was added water, and extraction was made with methylene chloride. The organic layer was concentrated under reduced pressure, and the residue thus obtained was chromatographed on silica gel column. There was obtained 263 mg of 1-[5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl]-4-(methylaminocarbonylmethyl)-piperazine. Spectrophotometric data of the product support the structure of the formula (V) shown below. ##STR5##

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. additionTo the reaction mixture was added
  3. extractionwater, and extraction
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained
  6. customwas chromatographed on silica gel column

Sources & evidence

ORD record
ord-253f5fbbf2084f0f95c1c0e20c2f9ce3
Source dataset
uspto-grants-1987_04
Patent number
US04656172

Linked notes

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