Benzhydrol → 4-((Diphenylmethoxy)methyl)piperidine

HRID 565639Notes

Reaction equation

HRID 565639 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.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21]O)[CH2:17][CH2:16]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:14][CH2:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7037BenzhydrolHCID 14798Sodium HydroxideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 4207714-Piperidinemethanol

Product 1

HCID 27624204-((Diphenylmethoxy)methyl)piperidineYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a reactor fitted with a water trap, a mixture of benzhydrol (3.7 g), 4-piperidinemethanol (2.3 g), camphor-10-sulfonic acid (7.0 g), and toluene (30 mL) was refluxed for 2 hours. After cooling, 35 mL of 1N-aqueous sodium hydroxide was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure to provide 5.3 g of the title compound. Yield 94%. This product was not further purified but directly submitted to the next reaction.

Workup

  1. customIn a reactor fitted with a water trap
  2. temperaturewas refluxed for 2 hours
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffaa66633f364377b4f75262acee6899
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

Loading…