Trifluoroacetic acid → 3-[(Diphenylmethoxy)methyl]piperidine

HRID 2225437Notes

Reaction equation

HRID 2225437 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1.[CH:16](O)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:17]1([CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7037BenzhydrolHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 190042093-[(Diphenylmethoxy)methyl]piperidineYield 30.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added cautiously to a vigorously stirred solution of piperidine-3-methanol (5.75 g, 50 mmol) in dichloromethane (20 ml) and the mixture treated with benzhydrol (9.2 g, 50 mmol) portionwise over 5 minutes, stirred at room temperature for 2 hours and evaporated. The residue was dissolved in dioxane (50 ml) and the solution treated with 4M aqueous sodium hydroxide solution (100 ml), stirred at room temperature for 2 hours, diluted with ether and water and the layers separated. The organic layer was washed with water and extracted into 2M hydrochloric acid. The acidic extract was washed with ether, basified with solid sodium carbonate, extracted into ether, washed with water, dried over magnesium sulphate and evaporated to give the title compound (4.31 g) as a pale yellow oil which was characterised by its 1H-NMR spectrum.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dioxane (50 ml)
  3. additionthe solution treated with 4M aqueous sodium hydroxide solution (100 ml)
  4. stirringstirred at room temperature for 2 hours
  5. additiondiluted with ether and water
  6. customthe layers separated
  7. washThe organic layer was washed with water
  8. extractionextracted into 2M hydrochloric acid
  9. extractionThe acidic extract
  10. washwas washed with ether
  11. extractionextracted into ether
  12. washwashed with water
  13. dry with materialdried over magnesium sulphate
  14. customevaporated

Sources & evidence

ORD record
ord-844e1dc3ed924f268f95eb8245157dc9
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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