Isopropylamine → [6-(dimethylamino)hexyl]-4,5-diphenyl-1H-pyrazole-1-acetamide

HRID 704824

Reaktionsgleichung

Reaktionsgleichung von HRID 704824
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([O:21]CC)=O)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]N)[CH3:26].C([N:37](C(C)C)CC)(C)C.C(N)(C)C>C(Cl)(Cl)Cl.CCOCC>[CH3:24][N:25]([CH3:26])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]([CH2:18][C:19]([NH2:37])=[O:21])[N:9]=1

Komponenten

7

Edukt 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2585446-(Dimethylamino)hexylamine2×HCID 146995514,5-Diphenyl-1-(ethoxycarbonylmethyl)-pyrazole

Produkt 1

HCID 86743406[6-(dimethylamino)hexyl]-4,5-diphenyl-1H-pyrazole-1-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 8 g (0.026 mol) of ethyl 4,5-diphenyl-1H-pyrazole-1-acetate of Example 1, 4.1 g (0.028 mol) of dimethylaminohexylamine and 33.3 mL (0.19 mol) of diisopropylethylamine was stirred on a steam bath under nitrogen for 18 hours. Thin layer chromatography on silica gel with 5% isopropylamine in chloroform showed incomplete reaction. Another 1 mL of dimethylaminohexylamine was added and stirring continued on a steam bath for an additional 24 hours. The reaction was stripped in vacuo, taken up in 200 mL of ether, washed two times with water, washed once with half saturated sodium bicarbonate solution, washed with water again, washed with saturated sodium chloride solution, dried over magnesium sulfate, treated with decolorizing carbon, filtered and stripped. The residue was taken up in ether and treated with a slight excess of hydrochloric acid. The hydrochloride salt was extracted into water and washed three times with ether; the water layer was chilled, and made basic with solid sodium carbonate and extracted two times with ether. The ether extracts were combined, washed once with saturated sodium chloride, dried over magnesium sulfate, treated with decolorizing carbon, filtered and stripped. The resulting residue was triturated in pentane to yield 4.14 g of N-([6-(dimethylamino)hexyl]-4,5-diphenyl-1H-pyrazole-1-acetamide, mp 60°-63° C.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued on a steam bath for an additional 24 hours
  3. washwashed two times with water
  4. washwashed once with half saturated sodium bicarbonate solution
  5. washwashed with water again
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with decolorizing carbon
  9. filtrationfiltered
  10. additiontreated with a slight excess of hydrochloric acid
  11. extractionThe hydrochloride salt was extracted into water
  12. washwashed three times with ether
  13. temperaturethe water layer was chilled
  14. extractionextracted two times with ether
  15. washwashed once with saturated sodium chloride
  16. dry with materialdried over magnesium sulfate
  17. additiontreated with decolorizing carbon
  18. filtrationfiltered
  19. customThe resulting residue was triturated in pentane

Quellen und Nachweise

ORD-Eintrag
ord-0bc021e3ff9f4c52a05e235ade8baba8
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988725

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