Ethanolamine → HCID 68990855, compound

HRID 749172Notes

Reaction equation

HRID 749172 reaction equation
Br[CH2:2][CH:3]1[O:7][CH2:6][CH2:5][O:4]1.[CH2:8]([CH2:10][NH2:11])[OH:9].C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1>[NH3:11].[O:4]1[CH2:5][CH2:6][O:7][CH:3]1[CH2:2][NH:11][CH2:10][CH2:8][OH:9]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 780681,3-Dioxolane, 2-(bromomethyl)-

Product 2

HCID 222AmmoniaHCID 68990855HCID 68990855, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(bromomethyl)-1,3-dioxolane (4.4 ml, 42.5 mmol) in dioxane (60 ml) was reacted with ethanolamine (4 ml, 66.3 mmol) in the presence of potassium carbonate (6.9 g, 50 mmol) at 75° C. for 7 hours. The mixture was concentrated and purified by chromatography on silica gel, eluting with dichloromethane:methanol (97:3) then dichloromethane:methanolic ammonia (94:6), to yield 2-((1,3-dioxolan-2-ylmethyl)amino)ethanol (1.90 g, 24% yield):

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel
  3. washeluting with dichloromethane:methanol (97:3)

Sources & evidence

ORD record
ord-8cf3b8d623904753a1344bcb93b9e675
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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