Diethanolamine → Methyl 4-[N,N-bis(2-hydroxyethyl)aminomethyl]benzoate

HRID 1458680Notes

Reaction equation

HRID 1458680 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[NH:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16]>C(Cl)(Cl)Cl>[OH:16][CH2:15][CH2:14][N:13]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 36664Methyl 4-(chloromethyl)benzoate

Product 1

HCID 22371208Methyl 4-[N,N-bis(2-hydroxyethyl)aminomethyl]benzoateYield 64.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.7 g (9.2 mmol) of methyl 4-chloromethylbenzoate in 25 ml of chloroform was added with 10 g (95 mmol) of diethanolamine, followed by heating under reflux for 10 hours. The resulting solution was washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform), whereby 1.5 g of a colorless oil were obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 10 hours
  3. washThe resulting solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (chloroform)

Sources & evidence

ORD record
ord-3158d4fe330b4f58920a14a96c624adf
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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