Ethanolamine → 2-(4-Dimethylamino-benzylamino)-ethanol

HRID 1641111Notes

Reaction equation

HRID 1641111 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1C=O.[CH2:12]([CH2:14][NH2:15])[OH:13].[C:16](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CCO.O>[CH3:11][N:2]([CH3:1])[C:3]1[CH:4]=[CH:7][C:8]([CH2:16][NH:15][CH2:14][CH2:12][OH:13])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 34289Benzaldehyde, (dimethylamino)-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 4112772-(4-Dimethylamino-benzylamino)-ethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(dimethylamino)benzaldehyde (0.50 g, 3.35 mmol) and ethanolamine (0.409 g, 6.7 mmol) in anhydrous EtOH (13 mL) was stirred at rt for 17 hours before sodium triacetoxyborohydride (1.42 g, 6.7 mmol) was added. The reaction mixture was stirred for 4.5 hours, added water, and the pH was adjusted to 12 with 5 M NaOH. The mixture was extracted with EtOAc, and the organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of DCM:MeOH 9:1 to 1:1, to provide the desired product 2-(4-(dimethylamino)benzylamino)ethanol (51A).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography on silica gel eluting with a gradient of DCM:MeOH 9:1 to 1:1

Sources & evidence

ORD record
ord-c3c1f1cc3b8d4bb3b0dd939d637c97a0
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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