Sodium Bicarbonate → 4-[2-[4-(4-fluorobenzoyl)-1-piperidyl]ethyl]-6-methoxy-2(1H)-quinolone hydrochloride

HRID 619113Notes

Reaction equation

HRID 619113 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6](=[O:16])[CH:5]=1.[F:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>C(#N)C>[ClH:1].[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=4)[NH:7][C:6](=[O:16])[CH:5]=3)[CH2:26][CH2:25]2)=[O:23])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 153886994-(2-chloroethyl)-6-methoxy-2(1H)-quinolone

Product 1

HCID 218460534-[2-[4-(4-fluorobenzoyl)-1-piperidyl]ethyl]-6-methoxy-2(1H)-quinolone hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.1 g (4.6 mmol) of 4-(2-chloroethyl)-6-methoxy-2(1H)-quinolone, 1.0 g (5.5 mmol) of 4-(4-fluorobenzoyl)piperidine and 0.38 g (4.6 mmol) of sodium hydrogen carbonate in 20 ml of acetonitrile is heated to reflux for 8.5 hours. The reaction medium is then evaporated to dryness and the crude product is purified by flash chromatography on silica, eluting with a methanol/dichloromethane (5:95) mixture containing traces of aqueous ammonia.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 8.5 hours
  3. customThe reaction medium is then evaporated to dryness
  4. customthe crude product is purified by flash chromatography on silica
  5. washeluting with a methanol/dichloromethane (5:95) mixture
  6. additioncontaining traces of aqueous ammonia

Sources & evidence

ORD record
ord-f57cf540ea5b424981c2b0e5493f4ec0
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

Loading…