Morpholine → 2-Morpholinoethanol

HRID 56259Notes

Reaction equation

HRID 56259 reaction equation
Br[CH2:2][CH2:3][OH:4].[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[O:4]1[CH2:9][CH2:10][N:5]([CH2:6][CH2:7][OH:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 611632-MorpholinoethanolYield 83.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromoethanol (27.9 g, 223 mmol), morpholine (40 g, 459 mmol) and K2CO3 (48.4 g, 350 mmol) in CH3CN (30 mL) was refluxed for 3 h. The mixture was then cooled to rt and filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (24.40 g, 83%), which was used for next step without further purification.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f20fb319d6d84aee82afcd249a5faeb9
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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