Benzyl Bromide → 2,2'-((Phenylmethyl)imino)bisethanol

HRID 1479308Notes

Reaction equation

HRID 1479308 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:18]([CH2:22][CH2:23][OH:24])[CH2:19][CH2:20][OH:21]>C(Cl)(Cl)Cl>[CH2:10]([N:18]([CH2:22][CH2:23][OH:24])[CH2:19][CH2:20][OH:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8113DiethanolamineHCID 81531Diisopropylethylamine

Product 1

HCID 75532,2'-((Phenylmethyl)imino)bisethanolYield 79.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Diisopropylethylamine (2.99 mL, 17.1 mmol) and benzyl bromide (1.36 mL, 11.4 mmol) were added to a chloroform (46 mL) solution of diethanolamine (1.80 g, 17.1 mmol), and the solution was stirred for 5 hours under heat and reflux. The reaction solution was washed with water, saturated sodium bicarbonate water, and saturated brine, dried over magnesium sulfate, and evaporated after filtration. The resulting residue was purified by silica gel column chromatography (methanol/chloroform=0/100 to 12/88) to give N-benzyldiethanolamine (1.77 g, 79.4%).

Workup

  1. temperatureunder heat
  2. temperaturereflux
  3. washThe reaction solution was washed with water, saturated sodium bicarbonate water, and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. filtrationafter filtration
  7. customThe resulting residue was purified by silica gel column chromatography (methanol/chloroform=0/100 to 12/88)

Sources & evidence

ORD record
ord-4554cc8b7fb44a449edbd5f942159070
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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