Oxalic Acid → HCID 20344002, compound

HRID 2049879Notes

Reaction equation

HRID 2049879 reaction equation
[CH2:1]([C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4])[CH3:2].Cl[CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][O:27]1.C(=O)(O)[O-].[Na+].[I-].[K+].[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40]>CN(C)C=O.O.CCOCC>[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40].[CH2:1]([C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:6][CH2:7][N:8]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][O:27]2)[CH2:9][CH2:10]1)=[O:4])[CH3:2]

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 181502-Chloromethyl tetrahydrofuranHCID 516892Sodium BicarbonateHCID 20343999HCID 20343999, compound

Product 1

HCID 20344002HCID 20344002, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.8 g of 4-ethylcarbonyl-4-(2-phenylthiophenyl)piperidine, free base of Example 11, 0.93 g of 2-chloromethyltetrahydrofuran, 1.6 g of sodium bicarbonate and 1.6 g of potassium iodide in 20 ml of dimethylformamide is stirred at 80°-85° C. for 16 hours. Thereafter, the mixture is permitted to cool before being diluted with 50 ml of water. The diluted mixture is extracted four times with 30 ml portions of ether and the combined ether extracts are washed with 25 ml saturated sodium chloride solution and then dried. The resulting oil product is chromatographed (alumina column, 10% methyl alcohol in ether eluant) to provide a purified product which, in ether, is converted to its oxalic acid salt. The salt is washed well with ether, dried under vacuum, recrystallized from a methanol-acetone-ether mixture and washed with ether to provide 4-ethylcarbonyl-4-(2-phenylthiophenyl)-1-(2-tetrahydrofurylmethyl)piperidine oxalate.

Workup

  1. temperatureto cool
  2. extractionThe diluted mixture is extracted four times with 30 ml portions of ether
  3. washthe combined ether extracts are washed with 25 ml saturated sodium chloride solution
  4. customdried
  5. customThe resulting oil product is chromatographed (alumina column, 10% methyl alcohol in ether eluant)
  6. customto provide a purified product which
  7. washThe salt is washed well with ether
  8. customdried under vacuum
  9. customrecrystallized from a methanol-acetone-ether mixture
  10. washwashed with ether

Sources & evidence

ORD record
ord-058249f641e241c9ba9d4de5c3e59db2
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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