Piperidin-4-ol → HCID 70648009, compound

HRID 2202586Notes

Reaction equation

HRID 2202586 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[O:10][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 521998p-Toluenesulfonic acid monohydrateHCID 61100554HCID 61100554, compound

Product 1

HCID 70648009HCID 70648009, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Molecular sieves, (2,4-difluorophenyl)phenylmethanol (3.69 g, 16.8 mmol), and p-toluenesulfonic acid monohydrate (3.84 g, 20.2 mmol) were added to a suspension of 4-hydroxypiperidine (1.7 g, 16.8 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 (2.8 g, 54.9%) 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-10e749bd810a49a3876611c2992a9149
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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