Ethanolamine → 2-[(4-Methoxybenzyl)amino]ethanol

HRID 577574Notes

Reaction equation

HRID 577574 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][CH2:12][CH2:13][OH:14].C([O-])(O)=O.[Na+].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][CH2:12][CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 1044692-[(4-Methoxybenzyl)amino]ethanolYield 149.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 4-methoxybenzaldehyde (10 g, 74 mmol), 2-aminoethanol (4.9 g, 81 mmol) and NaHCO3 (9.3 g, 110 mmol) in MeOH (100 mL) was refluxed for 3 hours. The reaction mixture was cooled to 15° C. To the mixture was added portionwise NaBH4 (3.3 g, 88 mmol) at 15° C. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give 2-[(4-methoxybenzyl)amino]ethanol (130a, 20 g) as a brown oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d1329c4d7acf455e845e28318edf8655
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…