Benzyl Bromide → HCID 22132581, compound

HRID 1856762Notes

Reaction equation

HRID 1856762 reaction equation
[CH:1]1([NH:7][CH2:8][CH:9]([OH:12])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH:1]1([NH:7][CH2:8][CH:9]([O:12][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 419885HCID 419885, compound

Product 1

HCID 22132581HCID 22132581, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-cyclohexyl-N-(2-hydroxybutyl)amine (49.2 g) in tetrahydrofuran (1 liter) is added with stirring sodium hydride (60% oily dispersion, 12.6 g) in portions at 0° C. The mixture is stirred at the same temperature for one hour, and thereto is added dropwise benzyl bromide (34 ml). The mixture is stirred at room temperature overnight, and the mixture is concentrated under reduced pressure to remove the solvent. To the residue is added water, and the mixture is extracted with chloroform. The extract is dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=200:10:1) to give N-cyclohexyl-N-(2-benzyloxybutyl)amine (25.8 g) as a colorless oil.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. additionTo the residue is added water
  5. extractionthe mixture is extracted with chloroform
  6. dry with materialThe extract is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=200:10:1)

Sources & evidence

ORD record
ord-157211aa10e5451f907f2d403b48571b
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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