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

HRID 2178276Notes

Reaction equation

HRID 2178276 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 it 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 pH1 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-15098c6243604b76b975163d48594892
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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