Sodium Iodide → 4-(Diphenylmethoxy)-1-piperidinehexanol

HRID 1067580Notes

Reaction equation

HRID 1067580 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][CH2:25][CH2:26][CH2:27][OH:28].[I-].[Na+].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][CH2:25][CH2:26][CH2:27][OH:28])[CH2:11][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 229893784-(Diphenylmethoxy)-1-piperidinehexanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.00 g of 4-(diphenylmethoxy)piperidine was dissolved in 10 ml of N,N-dimethylformamide; 0.49 ml of 6-bromo-hexanol, 0.56 g of sodium iodide and 0.62 g of potassium carbonate were added, followed by stirring at 100° C. for 1 hour. Ice water was added, followed by extraction with ethyl ether; 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 1.24 g of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl ether
  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-b8e21c2d622544a5b05ae16f00debb01
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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