Potassium Iodide → 5[[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]methyl]-3-methyl-2-oxazolidinone

HRID 476939Notes

Reaction equation

HRID 476939 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][CH:25]1[O:29][C:28](=[O:30])[N:27]([CH3:31])[CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[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][CH:25]3[O:29][C:28](=[O:30])[N:27]([CH3:31])[CH2:26]3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 128899255-(Chloromethyl)-3-methyl-2-oxazolidinone

Product 1

HCID 146987685[[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]methyl]-3-methyl-2-oxazolidinoneYield 24%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared according to the procedure of Example 1. A mixture of 4.6 g (0.015 mole) of α,α-bis-(p-fluorophenyl)-4-piperidinemethanol, 2.2 g (0.015 mole) of 5-(chloromethyl)-3-methyl-2-oxazolidinone, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 100 ml of 1-butanol gave a gum as residue. The gum was purified by column chromatography on 50 g of Florisil®. Fractions eluted with 5-20% acetone in benzene were combined and concentrated to give a solid residue. The solid was recrystallized from isopropyl ether-2-propanol to yield 1.5 g (24%) of white solid, m.p. 147°-148° C.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customThe gum was purified by column chromatography on 50 g of Florisil®
  4. washFractions eluted with 5-20% acetone in benzene
  5. concentrationconcentrated
  6. customto give a solid residue
  7. customThe solid was recrystallized from isopropyl ether-2-propanol

Sources & evidence

ORD record
ord-11e57a56b1714020aa059ce3caf9c217
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

Loading…