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

HRID 476937Notes

Reaction equation

HRID 476937 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][CH2:26][CH:27]1[O:31][C:30](=[O:32])[N:29]([CH3:33])[CH2:28]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]>C(O)CCC>[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[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][CH2:26][CH:27]3[O:31][C:30](=[O:32])[N:29]([CH3:33])[CH2:28]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 198114995-(3-Chloropropyl)-3-methyl-2-oxazolidinone

Product 1

HCID 146987655-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propyl]-3-methyl-2-oxazolidinone oxalateYield 54%

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, 2.7 g (0.015 mole) of 5-(3-chloropropyl)-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 converted to the oxalic acid salt and the solid was recrystallized from absolute ethanol to yield 4.5 g (54%) of white solid, m.p. 150°-153° C., with decomposition.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customthe solid was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-092f4d497e70490db3187db7f856d912
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

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