Hydrochloric Acid → HCID 69408864, compound

HRID 1349432Notes

Reaction equation

HRID 1349432 reaction equation
C[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)(C)C.C(C1C=CC(CCl)=CC=1)=C.[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.Cl>N1C=CC=CC=1N1CCNCC1.CO>[CH:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:2][N:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)=[CH:27][CH2:28]2)=[CH:10][CH:9]=1)=[CH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 156274-tert-ButylstyreneHCID 705171-(4-Pyridyl)piperazineHCID 74126p-Vinylbenzyl chloride2×

Product 1

HCID 69408864HCID 69408864, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 944591-(2-Pyridyl)piperazineCatalystHCID 887MethanolSolvent

Procedure

Dye-labeled poly(4-tert-butylstyrene)-supported pyridylpiperazine catalyst for the acylation of phenols. 4-Vinylbenzylchloride was passed through neutral alumina to remove any inhibitors. 1-(4-Vinylbenzyl)-4-pyridylpiperazine was prepared by dissolving 4.32 mL of 4-vinylbenzylchloride and 10 g of N-(4-pyridyl)piperazine in 100 mL of methanol. The solution was allowed to reflux overnight. After cooling to room temperature, 20 mL of 6 N HCl was added and the solution was extracted three times with ether. The ether extracts were discarded and 20 g of NaOH in 20 mL of water was added dropwise to the aqueous solution. The resulting precipitate was recovered by filtration and purified by column chromatography using 5% triethylamine in ethyl acetate as the eluent. Removal of the solvent under reduced pressure produced the product in 72.1% yield. 1H NMR: δ 8.2 (d, 6.6 Hz, 2H), 7.3 (dd, J=6.4, 6.6 Hz, 4H), 6.7 (dd, J=10.7, 17.6 Hz, 1H), 6.6 (d, 6.4 Hz, 2H), 5.7 (d, 17.6 Hz, 1H), 5.2 (d, 10.7 Hz, 1H), 3.5 (s, 1H), 3.3 (t, 5.2 Hz, 4H), 2.5 (t, 5.1 Hz, 4H). 13C NMR: δ 155.2, 150.4, 137.6, 136.9, 136.7, 130.0, 126.4, 113.9, 108.5, 62.9, 52.7, 46.1.

Workup

  1. customto remove any inhibitors
  2. temperatureto reflux overnight
  3. extractionthe solution was extracted three times with ether
  4. addition20 g of NaOH in 20 mL of water was added dropwise to the aqueous solution
  5. filtrationThe resulting precipitate was recovered by filtration
  6. custompurified by column chromatography
  7. customRemoval of the solvent under reduced pressure
  8. customproduced the product in 72.1% yield

Sources & evidence

ORD record
ord-cfccc8c8a69646fe9e9d7f3d79a28510
Source dataset
uspto-grants-2007_05
Patent number
US07211705B2

Reaction notes

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