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

HRID 27783Notes

Reaction equation

HRID 27783 reaction equation
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

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 656601Procaterol HCl

Product 1

HCID 233420445-(1-Cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyrilYield 136.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a30b912252274da2a1549b9cd6b34979
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

Loading…