Triethylamine → 1-Benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazine

HRID 414489Notes

Reaction equation

HRID 414489 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]([OH:19])=O.C(N(CC)CC)C.C(C(Cl)=O)C.[CH:32]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.C(OCC)(=O)C.CCCCCC.O>[CH:32]([N:45]1[CH2:50][CH2:49][N:48]([C:17](=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][C:4]2[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=2[O:2][CH3:1])[CH2:47][CH2:46]1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 70048BenzhydrylpiperazineHCID 538241405-(2,3,4-Trimethoxyphenyl)-2,4-pentadienoic acid

Product 1

HCID 538213461-Benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazineYield 72.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

To 7.3 g (27.6 mmol) of 5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoic acid were added 300 ml of dry dichloromethane and 3.85 ml (27.6 mmol) of triethylamine, and the mixture was stirred at 0° C. To the resulting mixture was added 2,64 ml (27,6 mmol) of ethylcarbonyl chloride followed by stirring for 1 hour. To the mixture was added 8.36 g (33 mmol) of benzhydrylpiperazine in 50 ml of dry dichloromethane. Temperature of the mixture was raised to room temperature followed by stirring for additional 16 hours. After addition of water, the mixture was extracted with dichloromethane. The organic layer was washed successively with aqueous 1N-hydrochloric acid solution, a saturated aqueous sodium chloride solution and a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. There was obtained a residue, which was subjected to column chromatography on silica gel to give 10.0 g (20.1 mmol) of 1-benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazine from eluates of ethyl acetate-hexane (1:1).

Workup

  1. stirringby stirring for 1 hour
  2. temperatureTemperature of the mixture was raised to room temperature
  3. stirringby stirring for additional 16 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe organic layer was washed successively with aqueous 1N-hydrochloric acid solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThere was obtained a residue, which

Sources & evidence

ORD record
ord-7ce10c6f5a344654906c2455d051c4ad
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Reaction notes

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