Hydrochloric Acid → Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate

HRID 395004Notes

Reaction equation

HRID 395004 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][CH2:15][C:16]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1)=[CH:10][CH:9]=[CH:8][CH:7]=2>O1CCOCC1.C(OCC)C>[F:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][CH2:15][C:16]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69682605Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

Product 1

HCID 22469283Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylateYield 69.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

50 cm3 of a solution of hydrogen chloride in dioxane at a concentration of 4M were added cautiously to a solution of 8.7 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate in 150 cm3 of anhydrous dioxane, and the temperature was maintained below 30° C. during the addition. After stirring for 18 hours in the region of 20° C., the suspension was diluted with 250 cm3 of diethyl ether, filtered and washed with 5 times 50 cm3 of diethyl ether, and the solid was dried in a desiccator under reduced pressure (2 kPa) and at a temperature in the region of 20° C. The solid was taken up in 50 cm3 of water and aqueous 5N sodium hydroxide solution was added so that the pH was at about 10, and the mixture was then extracted with 5 times 100 cm3 of diethyl ether. The organic phases were combined, dried over magnesium sulfate, taken up with plant charcoal (3S), filtered and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C. 4.7 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate were obtained in the form of a viscous orange-colored oil.

Workup

  1. temperaturethe temperature was maintained below 30° C. during the addition
  2. filtrationfiltered
  3. washwashed with 5 times 50 cm3 of diethyl ether
  4. customthe solid was dried in a desiccator under reduced pressure (2 kPa) and at a temperature in the region of 20° C
  5. additionaqueous 5N sodium hydroxide solution was added so that the pH
  6. extractionthe mixture was then extracted with 5 times 100 cm3 of diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C

Sources & evidence

ORD record
ord-08e9ea38cf5b4aa4975d99ec5a7f8004
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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