Benzyl Bromide → 2-(1-Benzylpiperidin-2-yl)ethan-1-ol

HRID 538680Notes

Reaction equation

HRID 538680 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 151442-Piperidin-2-ylethanol

Product 1

HCID 102425512-(1-Benzylpiperidin-2-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of piperidine-2-ethanol (20 g, 155 mmol) in ethanol (240 mL) was added K2CO3 (106 g, 775.1 mmol) followed by addition of benzyl bromide (18.4 mL, 155.04 mmol) at 0° C. The reaction mixture was stirred at rt overnight, filtered through a sintered funnel and concentrated. The crude material was dissolved in ethyl acetate, the organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to get liquid compound 49.

Workup

  1. filtrationfiltered through a sintered funnel
  2. concentrationconcentrated
  3. dissolutionThe crude material was dissolved in ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8d761a23fb7743ddb3bb6b93c5fa14c2
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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