Oxalic Acid → 5-[1,1-Diphenyl-3-(4-phenylpiperidino)propyl]-2-methyl-1,3,4-oxadiazole oxalate

HRID 972551Notes

Reaction equation

HRID 972551 reaction equation
[C:1]1([C:7]([C:28]2NN=[N:30][N:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].N1C=CC=CC=1.[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48]>CCOCC.CO>[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48].[C:1]1([C:7]([C:28]2[O:35][C:33]([CH3:34])=[N:30][N:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][CH2:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178420099HCID 178420099, compound

Product 1

HCID 214047955-[1,1-Diphenyl-3-(4-phenylpiperidino)propyl]-2-methyl-1,3,4-oxadiazole oxalate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

2.0 Parts of 5-[1,1-diphenyl-3-(4-phenylpiperidino)propyl]-1H-tetrazole hemimethanolate, 6.21 parts of acetic anhydride and 20 parts by volume of pyridine are heated together to reflux for 1 hour and 20 minutes. The mixture is then cooled and stripped in vacuum. The resulting residue is taken up in ether. The ether solution is washed with sodium hydroxide, dried over sodium sulfate and then stripped in vacuum to give a gum. 1.74 Parts of this gum dissolved in 6 parts by volume of methanol and 0.35 part of oxalic acid dissolved in 4 parts by volume of methanol are mixed together. This solution is diluted with ether to just below the point of cloudiness. The crystals which form are filtered off and dried in vacuum to provide 5-[1,1-diphenyl-3-(4-phenylpiperidino)propyl]-2-methyl-1,3,4-oxadiazole oxalate, melting at 180° - 190° C., having the following formula ##STR9##

Workup

  1. temperatureto reflux for 1 hour and 20 minutes
  2. temperatureThe mixture is then cooled
  3. washThe ether solution is washed with sodium hydroxide
  4. dry with materialdried over sodium sulfate
  5. customto give a gum
  6. additionare mixed together
  7. filtrationThe crystals which form are filtered off
  8. customdried in vacuum

Sources & evidence

ORD record
ord-b102d012895c4884826d2c524e8feded
Source dataset
uspto-grants-1977_10
Patent number
US04053477

Reaction notes

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