3-Bromobenzyl bromide → 184921-06-0

HRID 1291129Notes

Reaction equation

HRID 1291129 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br>CN(C)C=O>[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 79341Piperidin-4-ol

Product 1

HCID 765218184921-06-0Yield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.202 g (0.002 mol) of 4-hydroxypiperidine and 0.55 g (0.0022 mol) of 3-bromobenzyl bromide were dissolved in 5 ml of dimethylformamide and stirred at room temperature for 2 hrs. The solvent was distilled off and the residue was taken up in dichloromethane and washed with saturated bicarbonate solution and sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated. 0.52 g (96%) 1-(3-bromo-benzyl)-piperidin-4-ol was obtained as a brown oil. MS: me/e (% basic peak)=271, 269 (C12H16BrNO+, 26, 26.6), 270, 268 (25.5, 22), 171, 169 (47, 48.3), 114 (76.6), 100 (100).

Workup

  1. distillationThe solvent was distilled off
  2. washwashed with saturated bicarbonate solution and sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9bc74bbf57b4aff85256636a10ac1a1
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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