Cyclohexane → N,N-dibenzyl-2-bromoethanamine

HRID 244374Notes

Reaction equation

HRID 244374 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCCCC1.S(Br)([Br:27])=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][Br:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 22657Ethanol, 2-[bis(phenylmethyl)amino]-HCID 68176Thionyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 14378N,N-dibenzyl-2-bromoethanamineYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N,N-dibenzyl-2-aminoethanol (80.68 g) were added cyclohexane (500 ml) and DMF (12.9 ml), and thereto was added dropwise thionyl bromide (83.4 g). The mixture was stirred for 15 hours, and to the reaction solution was added an saturated aqueous sodium hydrogen carbonate solution in an ice-bath, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (72.1 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water (three times) and saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7475030529bf4ca69f9451befb6f5a98
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

Loading…