Potassium Carbonate → (S)-N-[[3-[3-fluoro-4-[4-(3-hydroxypropyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1078529Notes

Reaction equation

HRID 1078529 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[CH2:26][CH2:27][CH2:28][OH:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 10520848(S)-N-((3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Product 1

HCID 53923563(S)-N-[[3-[3-fluoro-4-[4-(3-hydroxypropyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.200 g, 0.595 mmol), 3-chloro-1-propanol (299 μL, 3.57 mmol) and potassium carbonate (0.493 g, 3.57 mmol) in acetonitrile (12 mL) was heated to reflux for 7 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude material was dissolved in 10% methanol/chloroform and absorbed onto silica gel (2 g). Chromatography of this material over silica gel (10 g), eluting with 1%, 3%, and then 6% methanol/chloroform, afforded, after concentration of appropriate fractions, 0.096 g (41%) of the title compound as a white solid with mp 154°-155.5° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material was dissolved in 10% methanol/chloroform
  5. customabsorbed onto silica gel (2 g)
  6. washChromatography of this material over silica gel (10 g), eluting with 1%, 3%
  7. custom6% methanol/chloroform, afforded

Sources & evidence

ORD record
ord-61f6163958ee4154b80b651d74152c55
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

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