Potassium Carbonate → 4-(Diphenylmethoxy)piperidinepropanol

HRID 397571Notes

Reaction equation

HRID 397571 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:22][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:15]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][N:12]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:11][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 229892644-(Diphenylmethoxy)piperidinepropanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.67 g of 4-diphenylmethoxypiperidine was dissolved in 20 ml of N,N-dimethylformamide; 1.09 ml of 3-bromopropanol and 1.66 g of potassium carbonate were added, followed by stirring at room temperature for 40 hours. After ice water was poured, the reaction mixture was extracted with ethyl acetate; the extract was washed with saline and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol-triethylamine (90:10:1). The desired fraction was collected and concentrated to yield 2.32 g of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. washeluted with ethyl acetate-methanol-triethylamine (90:10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-269e8d5a86fb4823a955dded40ff78c5
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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