Water → 2-[4-(7-chloro-4-quinolylamino)phenyl]-N-(1-ethyl-3-piperidyl)acetamide monohydrate

HRID 225130

Reaktionsgleichung

Reaktionsgleichung von HRID 225130
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][N:39]([CH2:43][CH3:44])[CH2:38]1.O>CS(C)=O>[OH2:22].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([NH:36][CH:37]4[CH2:42][CH2:41][CH2:40][N:39]([CH2:43][CH3:44])[CH2:38]4)=[O:23])=[CH:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 980943-amino-N-ethylpiperidineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 705973362-[4-(7-Chloro-4-quinolylamino)phenyl]acetic acid hydrochloride

Produkt 1

HCID 233290042-[4-(7-chloro-4-quinolylamino)phenyl]-N-(1-ethyl-3-piperidyl)acetamide monohydrateAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7.0 Grams (0.02 mole) of 2-[4-(7-chloro-4-quinolylamino)phenyl]acetic acid hydrochloride were dissolved in 150 milliliters of dimethyl sulphoxide by heating the stirred mixture to 100° C. under nitrogen. The solution was cooled to room temperature, 6.48 grams (0.04 mole) of carbonyl di-imidazole were added and the mixture was stirred for 21/2 hours under nitrogen. 7.68 Grams (0.06 mole) of 3-amino-1-ethylpiperidine were added, the solution was stirred for another 21/2 hours and poured into 500 milliliters of water. The mixture was refrigerated overnight and the resulting solid was broken up, stirred with water, collected and dried. The solid was dissolved in chloroform and chromatographed on an alumina column made up in chloroform. Elution with chloroform/methanol (4:1) gave 8.15 grams (92.5% yield) of 2-[4-(7-chloro-4-quinolylamino)phenyl]-N-(1-ethyl-3-piperidyl)acetamide monohydrate, melting point 160°-162° C.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. stirringthe solution was stirred for another 21/2 hours
  3. waitThe mixture was refrigerated overnight
  4. customcollected
  5. customdried
  6. dissolutionThe solid was dissolved in chloroform
  7. customchromatographed on an alumina column
  8. washElution with chloroform/methanol (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-eb994b99a963498aa299fb5d018646e3
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235908

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