Cyclopentanone → HCID 23151368, compound

HRID 2386943Notes

Reaction equation

HRID 2386943 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1>CO.[Cl-].[Zn+2].[Cl-].C([BH3-])#N.[Na+]>[CH:17]1([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 8452CyclopentanoneHCID 219186534-(4-Nitrophenoxy)piperidine

Product 1

HCID 23151368HCID 23151368, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3007855ZincchlorideSolventHCID 5003444Sodium cyanoborohydrideSolvent

Procedure

4-(4-nitrophenoxy)piperidine (1.03 g, 4.65 mmol) and cyclopentanone (783 mg, 9.31 mmol) were dissolved in a 0.5M methanol solution (20 mL) of zinc(II) chloride and sodium cyanoborohydride, and stirred at room temperature for 10 hours. The solvent was distilled off under reduced pressure, ethyl acetate and 1N sodium hydroxide aqueous solution were added, the mixture was extracted with ethyl acetate, and the organic phase washed with distilled water. After drying with anhydrous sodium sulfate, the product was concentrated, and the target compound (1.31 g, 96%) was thereby obtained as a light brown solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate and 1N sodium hydroxide aqueous solution
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic phase washed with distilled water
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. concentrationthe product was concentrated

Sources & evidence

ORD record
ord-5bab6e5080054a1bbc0c1a3a118f785a
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

Loading…