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Cyclohexanecarbonyl chloride → 5-(1-Cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril

HRID 27783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 27783
Cl.[OH:2][CH:3]([C:11]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:22])[NH:16]2)[CH:4]([NH:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH3:6].[CH:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>FC(F)(F)C(O)=O>[CH:23]1([C:29]([O:2][CH:3]([C:11]2[CH:20]=[CH:19][C:18]([O:21][C:3]([CH:11]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:12]3)=[O:2])=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:22])[NH:16]3)[CH:4]([NH:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH3:6])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 656601Procaterol HCl

Produkt 1

HCID 233420445-(1-Cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyrilAusbeute 136,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3.36 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril hydrochloride was dissolved in 20 ml of trifluoroacetic acid, and 8.8 g of cyclohexanecarboxylic acid chloride was added to the solution. The mixture was then heated at a temperature of 85° C. while refluxing. The reaction mixture was concentrated and diethyl ether was added to the residue to crystallize the product. The crystals thus obtained were separated by filtration and washed with diethyl ether. The resulting crystals were extracted successively with a saturated aqueous solution of sodium bicarbonate and chloroform, and the organic layer was washed with water, dried and concentrated to dryness. The resulting residue was crystallized from a mixture of diethyl ether and petroleum benzene to obtain 3.59 g of 5-(1-cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril having a melting point of 162° to 163° C. (after recrystallization from chloroform-n-hexane).

Aufarbeitung

  1. temperaturewhile refluxing
  2. concentrationThe reaction mixture was concentrated
  3. additiondiethyl ether was added to the residue
  4. customto crystallize the product
  5. customThe crystals thus obtained
  6. customwere separated by filtration
  7. washwashed with diethyl ether
  8. extractionThe resulting crystals were extracted successively with a saturated aqueous solution of sodium bicarbonate and chloroform
  9. washthe organic layer was washed with water
  10. customdried
  11. concentrationconcentrated to dryness
  12. customThe resulting residue was crystallized from a mixture of diethyl ether and petroleum benzene

Quellen und Nachweise

ORD-Eintrag
ord-a30b912252274da2a1549b9cd6b34979
Quelldatensatz
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04223137

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