2-Bromobenzyl bromide → HCID 677771, compound

HRID 1291126Notes

Reaction equation

HRID 1291126 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Br>CN(C)C=O>[Br:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 769652-Bromobenzyl bromideHCID 79341Piperidin-4-ol

Product 1

HCID 677771HCID 677771, compoundYield 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 2-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 sat. bicarbonate solution and sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated. 0.52 g (96%) of 1-(2-bromo-benzyl)-piperidin-4-ol was obtained as a brown oil. MS: me/e (% basic peak)=271, 269 (C12H16BrNO+, 53, 56), 270, 268 (66, 60), 171, 169 (86, 88), 114 (100), 100 (77).

Workup

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

Sources & evidence

ORD record
ord-b2952c84ccf24dabb07ed977e82ec477
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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