Potassium Iodide → Ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

HRID 394994Notes

Reaction equation

HRID 394994 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[CH:9][C:8]([O:26][CH3:27])=[CH:7][CH:6]=2.ClCCS[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[C:46](#N)[CH3:47]>>[CH:32]1([CH2:46][CH2:47][N:18]2[CH2:19][CH2:20][C:15]([CH2:14][CH2:13][CH2:12][C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([O:26][CH3:27])[CH:9]=4)[N:4]=[CH:3][C:2]=3[F:1])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:17]2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 22468445HCID 22468445, compoundHCID 22469748[(2-Chloroethyl)sulfanyl]cyclohexane

Product 1

HCID 22469603Ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

Conditions

Temperature
70 °C

Procedure

A mixture of 0.4 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate, 0.23 g of 2-chloroethylthiocyclohexane, 0.18 g of potassium iodide and 0.74 g of potassium carbonate in 15 cm3 of acetonitrile was stirred for 18 hours at a temperature in the region of 70° C. After cooling to about 20° C., the reaction mixture was concentrated to dryness under reduced pressure (5 kPa) at a temperature in the region of 40° C. The evaporation residue was purified by chromatography under atmospheric pressure, on a cartridge of silica gel (Bond Elut; particle size 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60° C. petroleum ether (8/2 by volume). The fractions containing the product were combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.32 g of ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate was obtained.

Workup

  1. temperatureAfter cooling to about 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (5 kPa) at a temperature in the region of 40° C
  3. customThe evaporation residue was purified by chromatography under atmospheric pressure, on a cartridge of silica gel (Bond Elut; particle size 70-200μ; mass 12 g)
  4. washeluting with a mixture of ethyl acetate/40-60° C. petroleum ether (8/2 by volume)
  5. additionThe fractions containing the product
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-7c98b954ee404ee0825fa8ea714afdad
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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