1,1'-Carbonyldiimidazole → (+/-)-Decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrroldinyl)-quinoline

HRID 1073143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073143
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[N:25]1([CH:30]2[CH:39]3[CH:34]([CH2:35][CH2:36][CH2:37][NH:38]3)[CH2:33][CH2:32][CH2:31]2)[CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:38]2[CH:39]3[CH:34]([CH2:33][CH2:32][CH2:31][CH:30]3[N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:35][CH2:36][CH2:37]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 13983380(+/-)-Decahydro-8-(-pyrrolidinyl)-quinoline

Produkt 1

HCID 13983383(+/-)-Decahydro-1-[(3,4-dichlorophenyl)-acetyl]-8-(1-pyrroldinyl)-quinolineAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 873 mg of 3,4-dichlorophenyl-acetic acid and 690 mg of carbonyldiimidazole in tetrahydrofuran was stirred for 1 hour at 20° to 25° C. and then 645 mg of the product of Step C in solution in 3 ml of tetrahydrofuran was added. After stirring for 4 hours at ambient temperature, the tetrahydrofuran was eliminated under reduced pressure at less than 40° C. and the residue was taken up in 20 ml of ether. The solution was washed with a saturated solution of sodium bicarbonate, then with water saturated with sodium chloride and the ethereal phase was dried and distilled to dryness under reduced pressure to obtain 1.39 g of the crude product.

Aufarbeitung

  1. customwas eliminated under reduced pressure at less than 40° C.
  2. washThe solution was washed with a saturated solution of sodium bicarbonate
  3. dry with materialwith water saturated with sodium chloride and the ethereal phase was dried
  4. distillationdistilled to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dac54359f17f470681159311f49ef8d9
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968700

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