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

HRID 2380694Notes

Reaction equation

HRID 2380694 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-a48de455c8834c80a17763d894bcd548
Source dataset
uspto-grants-1994_11
Patent number
US05369106

Reaction notes

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