Sodium Hydroxide → 4-Benzhydryloxypiperidine

HRID 2250415Notes

Reaction equation

HRID 2250415 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.O.C(OCC)(=O)C>[C:20]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10020094Ethyl 4-(diphenylmethoxy)piperidine carboxylate

Product 1

HCID 30175844-BenzhydryloxypiperidineYield 87.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(Diphenylmethoxy)-1-(ethoxycarbonyl)piperidine (4a) (11.45 g, 33.7 mmol) was dissolved in ethanol (72 mL). A cold solution of sodium hydroxide (8.2 g, 205 mmol) in water (12 mL) was added slowly and a small amount of heat was detected. The mixture was heated at reflux for 17 h and then cooled to room temperature. The mixture was subsequently diluted with water (100 mL) and ethyl acetate (100 mL) and stirred for 0.5 h to dissolve the resultant solid. The organic and aqueous layers were separated and the organic layer was washed with water (100 mL). The separate aqueous layers were extracted with ethyl acetate (100 mL) and the organic layers were combined, dried with Na2SO4, filtered and concentrated to yield 7.88 g (87.5%) of 5 as a viscous yellow oil. The structure was confirmed by 1H NMR.

Workup

  1. temperaturea small amount of heat
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 17 h
  4. dissolutionto dissolve the resultant solid
  5. customThe organic and aqueous layers were separated
  6. washthe organic layer was washed with water (100 mL)
  7. extractionThe separate aqueous layers were extracted with ethyl acetate (100 mL)
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb8c4749230452c9cedf835c15507d5
Source dataset
uspto-grants-2008_01
Patent number
US07317026B2

Reaction notes

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