Potassium Iodide → Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylate

HRID 1071253Notes

Reaction equation

HRID 1071253 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([CH2:16][CH2:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][C:20]=2[F:29])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[SH:35].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:29][C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:19]=1[CH2:18][CH2:17][CH2:16][C:8]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][S:35][C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)[CH2:6][CH2:7]1)=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 22468779Ethyl 1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate monohydrochloride

Product 1

HCID 22468562Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.8 g of ethyl 1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate monohydrochloride, 0.48 cm3 of thiophene-2-thiol, 2.8 g of potassium carbonate and 0.75 g of potassium iodide in 200 cm3 of anhydrous acetonitrile was stirred under an inert atmosphere for 18 hours at a temperature in the region of 70° C. After cooling to about 20° C., the suspension was filtered, washed with 3 times 30 cm3 of acetonitrile and the filtrate was then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C. The evaporation residue was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45μ; diameter 6 cm; height 30 cm), eluting with ethyl acetate and collecting 50-cm3 fractions. Fractions 25 to 52 were combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.3 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylate were obtained in the form of a viscous orange-colored oil.

Workup

  1. temperatureAfter cooling to about 20° C.
  2. filtrationthe suspension was filtered
  3. washwashed with 3 times 30 cm3 of acetonitrile
  4. concentrationthe filtrate was then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C
  5. customThe evaporation residue was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45μ; diameter 6 cm; height 30 cm)
  6. washeluting with ethyl acetate
  7. customcollecting 50-cm3 fractions
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-51b708deeb324bb68df77acdff1aa7ac
Source dataset
uspto-grants-2005_06
Patent number
US06903217B2

Reaction notes

Loading…