Oxalic Acid → 5-[2-[4[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]ethyl]-3-methyl-2-oxazolidinone oxalate

HRID 476934

Reaction equation

HRID 476934 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][CH:26]1[O:30][C:29](=[O:31])[N:28]([CH3:32])[CH2:27]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>C(O)CCC>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH:26]3[O:30][C:29](=[O:31])[N:28]([CH3:32])[CH2:27]3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 146987465-(2-Chloro-ethyl)-3-methyl-oxazolidin-2-one

Product 1

HCID 198367225-[2-[4[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]ethyl]-3-methyl-2-oxazolidinone oxalateYield 71%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of α,α-bis(p-fluorophenyl)-4-piperidinemethanol, 1.6 g (0.01 mole) of 5-(2-chloroethyl)-3-methyl-2-oxazolidinone, 5.3 g (0.085 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between water and benzene. The benzene layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a gum as residue. The gum was converted to the oxalic acid salt, recrystallizing from absolute ethanol to give 3.7 g (71%) of white powder, m.p. 124°-134° C. with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between water and benzene
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a gum as residue
  9. customrecrystallizing from absolute ethanol

Sources & evidence

ORD record
ord-e650102e8b3d4db68039db5dbc670305
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Linked notes

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