Triphenylphosphine → N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-piperidinoethyl)-5-isoquinolinesulfonamide

HRID 1090589

Reaktionsgleichung

Reaktionsgleichung von HRID 1090589
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH3:10])=[CH:4][CH:3]=1.[N:29]1([CH2:35][CH2:36]O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][N:13]([CH2:36][CH2:35][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:15])=[O:16])[CH3:10])=[CH:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53675817N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-5-isoquinolinesulfonamide

Produkt 1

HCID 53869192N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-piperidinoethyl)-5-isoquinolinesulfonamideAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.39 g of the amorphous compound obtained in Example 190, 0.145 g of 1-piperidinethanol and 0.369 g of triphenylphosphine in 5 ml of tetrahydrofuran, was added dropwise a solution of 0.245 g of diethyl azodicarboxylate in 2 ml of tetrahydrofuran with stirring under ice cooling. The mixture was stirred for 2 hours and evaporated to remove the solvent under a reduced pressure, and resulting residue dissolved in 30 ml of ethyl acetate and extracted three times with 10 ml of 1N hydrochloric acid. The aqueous layer was alkallized with sodium bicarbonate and extracted three times with 10 ml of ehtyl acetate, and the organic extract was dried over magnesium sulfate and evaporated to remove the solvent at a reduced pressure. The resulting residue was applied to a silica gel column and eluted with 2% methanol in chloroform, to obtain 0.37 g of the title compound as a colorless oil.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours
  2. customevaporated
  3. customto remove the solvent under a reduced pressure
  4. customresulting residue
  5. extractionextracted three times with 10 ml of 1N hydrochloric acid
  6. extractionextracted three times with 10 ml of ehtyl acetate
  7. extractionthe organic extract
  8. dry with materialwas dried over magnesium sulfate
  9. customevaporated
  10. customto remove the solvent at a reduced pressure
  11. washeluted with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-4b5fadd2e6704a4681297b884ba6b7c8
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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