Formic Acid → N-benzyl-N-methylaminoethanol

HRID 1440749Notes

Reaction equation

HRID 1440749 reaction equation
[CH2:1]([NH:8][CH:9]([OH:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12](O)=O.C=O>CO>[CH2:1]([N:8]([CH:9]([OH:11])[CH3:10])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 18470673N-benzyl-1-hydroxy-ethylamine

Product 1

HCID 19044148N-benzyl-N-methylaminoethanolYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture consisting of 151 g (1 mol) of N-benzylaminoethanol, 120 ml of 90% formic acid, 120 ml of a 35% aqueous formaldehyde solution and 1 liter of methanol is heated under reflux for 20 hours. The solvent is evaporated off in vacuo and the residue is treated with an aqueous sodium hydroxide solution and then extracted with methylene chloride. After customary treatment, the product is purified by distillation. 138 g of the desired product are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 20 hours
  3. customThe solvent is evaporated off in vacuo
  4. additionthe residue is treated with an aqueous sodium hydroxide solution
  5. extractionextracted with methylene chloride
  6. distillationAfter customary treatment, the product is purified by distillation

Sources & evidence

ORD record
ord-15ea540520bd48d89a3f6c1bf62a8a33
Source dataset
uspto-grants-1996_03
Patent number
US05500426

Reaction notes

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