Potassium Carbonate → 4-(Diphenylmethoxy)piperidinepropanol

HRID 1067578Notes

Reaction equation

HRID 1067578 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. Ice water was added, followed by extraction with ethyl acetate; the extract was washed with saline and dried with magnesium sulfate. After the dry product was concentrated 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. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saline
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter the dry product was concentrated 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-3186d48770514c6c804cdc98606160d7
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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