Benzhydrol → 4-Benzhydryloxypiperidine

HRID 2202574Notes

Reaction equation

HRID 2202574 reaction equation
[CH:1]([OH:14])([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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1(C)C=CC=CC=1>[CH:1]([O:14][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 79341Piperidin-4-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 30175844-BenzhydryloxypiperidineYield 50.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Molecular sieves, benzhydrol (1.1 g, 5.5 mmol), and p-toluenesulfonic acid monohydrate (1.0 g, 5.5 mmol) were added to a suspension of 4-hydroxypiperidine (505 mg, 5 mmol) in toluene, and the mixture was refluxed for 3 hours while removing water using a Dean-Stark condenser. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. From the reaction mixture, the insoluble matter was removed, and then the solvent was distilled off. The resulting residue was dissolved in ethyl acetate and washed with a 2-N sodium hydroxide solution 3 times. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off. Thus the title compound (676 mg, 50.6%) was obtained as an oily substance.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customwhile removing water using a Dean-Stark condenser
  3. customFrom the reaction mixture, the insoluble matter was removed
  4. distillationthe solvent was distilled off
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. washwashed with a 2-N sodium hydroxide solution 3 times
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b8d679ca075d4d11984b3adf250d847d
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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