Triethylamine → 1-[(E)-3-Phenyl-3-(4-pyridyl)acryloyl]-4-(3,4,5-trimethoxybenzoyl)piperazine

HRID 743034Notes

Reaction equation

HRID 743034 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24].[C:38]1(/[C:44](/[C:49]2[CH:54]=[CH:53][N:52]=[CH:51][CH:50]=2)=[CH:45]\[C:46](O)=[O:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C>C(Cl)Cl>[C:38]1(/[C:44](/[C:49]2[CH:54]=[CH:53][N:52]=[CH:51][CH:50]=2)=[CH:45]\[C:46]([N:28]2[CH2:29][CH2:30][N:25]([C:23](=[O:24])[C:22]3[CH:21]=[C:20]([O:19][CH3:18])[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=3)[CH2:26][CH2:27]2)=[O:47])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 28742041-(3,4,5-Trimethoxybenzoyl)piperazineHCID 67731480HCID 67731480, compound

Product 1

HCID 152305401-[(E)-3-Phenyl-3-(4-pyridyl)acryloyl]-4-(3,4,5-trimethoxybenzoyl)piperazineYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1 ml of a methylene chloride solution containing 0.330 g of diphenylphosphoryl azide and then 0.280 g of 1-(3,4,5-trimethoxybenzoyl)piperazine were added to 5 ml of a methylene chloride solution containing both 0.224 g of (E)-3-phenyl-3-(4-pyridyl)acrylic acid (prepared as described in Preparation 3) and 0.28 ml of triethylamine. The mixture was then stirred for 4 hours at room temperature, after which the reaction solution was diluted with 20 ml of methylene chloride. It was then washed with a 5% w/v aqueous solution of sodium bicarbonate, followed by a saturated aqueous solution of sodium chloride, and the organic phase was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the oily residue (0.686 g) was purified by silica gel flash chromatography. 0.419 g of the title compound was obtained as a white powder from the fractions eluted with mixtures of methylene chloride and methanol ranging from 100:2 to 100:3 by volume.

Workup

  1. washIt was then washed with a 5% w/v aqueous solution of sodium bicarbonate
  2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customthe oily residue (0.686 g) was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-be8b3d5bc6f1449ba5b6bab0281d4c08
Source dataset
uspto-grants-1996_09
Patent number
US05556852

Reaction notes

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