Benzyl Bromide → HCID 15892976, compound

HRID 1291193Notes

Reaction equation

HRID 1291193 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 15892976HCID 15892976, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.574 g (0.003 mol) of 1-benzyl-4-hydroxypiperidine dissolved in 5 ml of dimethylformamide was added dropwise at 0° to a suspension of 0.14 g (0.0035 mol) of sodium hydride in 5 ml of dimethylformamide. The mixture was left to warm to room temperature and was stirred for 1.5 hrs. Then, 0.39 ml (0.0033 mol) of benzyl bromide was added dropwise. The mixture was stirred at 40° for 18 hrs. The solvent was removed, the residue was taken up in water, adjusted to pH 11 with 2N aqueous NaOH and extracted with ether. The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.333 g (40%) of 1-benzyl-4-benzyloxypiperidine was obtained as a yellow oil. MS: me/e=282 (C9H24NO+).

Workup

  1. waitThe mixture was left
  2. stirringThe mixture was stirred at 40° for 18 hrs
  3. customThe solvent was removed
  4. extractionextracted with ether
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:1) as the eluent

Sources & evidence

ORD record
ord-c3e26ca1e1184d3fa847fed91ecdd763
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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