Hydrogen Bromide → 1-(4-Bromophenyl)piperidin-4-ol

HRID 57591Notes

Reaction equation

HRID 57591 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[BrH:19]>O>[Br:19][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 167921071-(4-Aminophenyl)piperidin-4-olHCID 23668193Sodium Nitrite

Product 1

HCID 235052161-(4-Bromophenyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-(4-aminophenyl)piperidin-4-ol (3.7 g, 319 mmol) in 60 mL of HBr 48%, a solution of NaNO2 (1.38 g, 20 mmol) in 15 mL of water was slowly added at 0° C. The mixture was stirred for 30 minutes and added to a solution of CuBr (1.57 g, 11 mmol) in 50 mL of HBr 48%. The resulting mixture was stirred and refluxed for 2 hours. The suspension thus obtained was partitioned between 2N NaOH and ethyl acetate. The organic layer was washed with aqueous NaCl, dried over Na2SO4 and concentrated to afford crude compound as grey solid 4.6 g. MS (m/z): 256 (M)+

Workup

  1. stirringThe resulting mixture was stirred
  2. temperaturerefluxed for 2 hours
  3. customThe suspension thus obtained
  4. customwas partitioned between 2N NaOH and ethyl acetate
  5. washThe organic layer was washed with aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e3d581441034e1da0235f7f7192df87
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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