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

HRID 1169114Notes

Reaction equation

HRID 1169114 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-1-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 acetate; the extract was washed with saline, dried over magnesium sulfate and 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 acetate
  2. washthe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated 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-f0df5a91f7a74e06ba38fbcc661e24ee
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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