Potassium Iodide → methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cycloheptylthio)ethyl]piperidine-3-carboxylate

HRID 2186370Notes

Reaction equation

HRID 2186370 reaction equation
[O:1]=[C:2]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][NH:8][CH2:7][C@@H:6]1[C:11]([O:13][CH3:14])=[O:12].[CH:27]1([S:34][CH2:35][CH2:36]Cl)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[O:1]=[C:2]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:36][CH2:35][S:34][CH:27]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:7][C@@H:6]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 224533722-Chloroethyl cycloheptyl sulfideHCID 53238173Methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate

Product 1

HCID 86758160methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cycloheptylthio)ethyl]piperidine-3-carboxylateYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
72 °C

Procedure

A mixture composed of 3.06 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate, 1.79 g of 2-chloroethyl cycloheptyl sulfide, 5.39 g of potassium carbonate, and 1.29 g of potassium iodide in 75 cm3 of acetonitrile was heated with stirring and under an inert atmosphere at a temperature in the region of 72° C. for 24 hours. After cooling to approximately 20° C., the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μ; diameter 4 cm; mass 150 g), elution was carried out with an ethyl acetate/methanol (95/5 by volume) mixture, and 50-cm3 fractions were collected. The fractions comprising the desired product were combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.6 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cycloheptylthio)ethyl]piperidine-3-carboxylate were obtained in the form of a viscous oil.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling to approximately 20° C.
  3. filtrationthe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  5. customThe residue obtained
  6. customwas purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μ; diameter 4 cm; mass 150 g), elution
  7. customwere collected
  8. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-6fbcb55b45d644b9a48a6d766fbe9a2e
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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