p-Toluenesulfonic acid → Benzyl [2-(4-benzhydrylpiperidino)-2-oxoethoxy]acetate

HRID 1395482Notes

Reaction equation

HRID 1395482 reaction equation
[CH:1]([CH:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:27])[CH2:21][O:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31](S(O)(=O)=O)=[CH:30][CH:29]=1>C(O)C1C=CC=CC=1>[CH:1]([CH:14]1[CH2:15][CH2:16][N:17]([C:20](=[O:27])[CH2:21][O:22][CH2:23][C:24]([O:26][CH2:38][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:18][CH2:19]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 196442Mcn 4308

Product 1

HCID 54337918Benzyl [2-(4-benzhydrylpiperidino)-2-oxoethoxy]acetate

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

In a similar operation, 3.63 grams (10 millimoles) of [2-(4-benzhydrylpiperidino)-2-oxoethoxy]acetic acid, 50 milliliters of benzyl alcohol and 150 milligrams of p-toluenesulfonic acid are mixed together and the resulting mixture heated at reflux temperature for about 6 hours to obtain a product in the reaction mixture. Thereafter, the reaction mixture subjected to reduced pressure to evaporate the alcohol and the residue is dissolved in benzene, the resulting solution washed with bicarbonate solution, dried and the solvent evaporated to obtain a benzyl [2-(4-benzhydrylpiperidino)-2-oxoethoxy]acetate product. The molecular weight of benzyl [2-(4-benzhydrylpiperidino)-2-oxoethoxy]acetate is 453.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux temperature for about 6 hours
  3. customto obtain a product in the reaction mixture
  4. customto evaporate the alcohol
  5. dissolutionthe residue is dissolved in benzene
  6. washthe resulting solution washed with bicarbonate solution
  7. customdried
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-f2d81979881a46fe8cff0aac2c8f1a3c
Source dataset
uspto-grants-1980_05
Patent number
US04203991

Reaction notes

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