Benzyl Bromide → (1-Benzylpiperidin-2-yl)methanol

HRID 538661Notes

Reaction equation

HRID 538661 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 2735486(1-Benzylpiperidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of piperidine-2-methanol (12; 6 g, 52.09 mmol) in dimethylformamide (DMF, 50 mL) were added successively K2CO3 (10.78 g, 78.14 mmol) and benzyl bromide (6.85 mL, 57.30 mmol) at 0° C. and the mixture stirred at rt for 16 hours. The reaction mixture was then filtered and the filtrate was concentrated. The residue was dissolved in EtOAc and the organic layer was washed with water and brine solution. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 30% EtOAc-hexane to provide compound 13.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe organic layer was washed with water and brine solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography on 230-400 mesh silica gel eluting with 30% EtOAc-hexane

Sources & evidence

ORD record
ord-f3b5f33e2aa04103be774d913a3b03ab
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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