Potassium Iodide → HCID 131723271, compound

HRID 2186352Notes

Reaction equation

HRID 2186352 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:13](=[O:26])[CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]1[C:22]([O:24][CH3:25])=[O:23].[CH:27]1[CH:32]=[C:31]([S:33][CH2:34][CH2:35]Cl)[CH:30]=[C:29]([F:37])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:37][C:29]1[CH:30]=[C:31]([S:33][CH2:34][CH2:35][N:19]2[CH2:20][CH2:21][C@@H:16]([CH2:15][CH2:14][C:13]([C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[O:26])[C@@H:17]([C:22]([O:24][CH3:25])=[O:23])[CH2:18]2)[CH:32]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 22453101HCID 22453101, compoundHCID 53238173(3R,4R)-methyl 4-(3-(6-methoxyquinolin-4-yl)-3-oxopropyl)piperidine-3-carboxylate

Product 1

HCID 131723271HCID 131723271, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6.44 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate in 100 cm3 of acetonitrile, 3.43 g of 2-(3-fluorophenylthio)ethyl-1-chloride, 8.85 g of potassium carbonate, and 1.24 g of potassium iodide was heated at a temperature in the region of 65° C. for 48 hours. After cooling, the insoluble material was filtered off. The filtrate was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The oily residue was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 6 cm; 250 g), elution was carried out with a dichloromethane/ethyl acetate/methanol (50/50/3 by volume) mixture, and 50-cm3 fractions were collected. The fractions from 19 to 25 were collected. These fractions were combined and then concentrated under reduced pressure (5 kPa) at approximately 40° C. 2.1 g of methyl (3R,4R)-1-[2-(3-fluorophenylthio)ethyl]-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate were obtained in the form of a mobile brown oil. Methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]-piperidine-3-carboxylate was prepared as described in Example 5.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble material was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  4. customThe oily residue was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 6 cm; 250 g), elution
  5. customwere collected
  6. customThe fractions from 19 to 25 were collected
  7. concentrationconcentrated under reduced pressure (5 kPa) at approximately 40° C

Sources & evidence

ORD record
ord-7926c977199846e69bcfd5d6f0f766fa
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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