Ethylene Oxide → 2-({[4-(Aminomethyl)cyclohexyl]methyl}amino)ethan-1-ol

HRID 259045

Reaction equation

HRID 259045 reaction equation
[CH:1]1([CH2:9][NH2:10])[CH2:6][CH2:5][CH:4]([CH2:7][NH2:8])[CH2:3][CH2:2]1.[CH2:11]1[O:13][CH2:12]1>CO>[OH:13][CH2:12][CH2:11][NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][NH2:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6354Ethylene Oxide2×HCID 173541,4-Cyclohexanedimethanamine

Product 1

HCID 203734282-({[4-(Aminomethyl)cyclohexyl]methyl}amino)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.2 gm. (0.1 mole) of 1,4-cyclohexanebis(methylamine) in 150 ml. anhydrous methyl alcohol and under an atmosphere of nitrogen is warmed to 45°-50° C. In a 20 minute period, there is introduced with good agitation and beneath the liquid surface a total of 1.1 gm. (0.025 mole) of ethylene oxide in gaseous form. The reaction temperature is maintained at 45°-50° C. for an additional one-half hour after stopping the addition of ethylene oxide. The methyl alcohol is removed by distillation at atmospheric pressure; excess 1,4-cyclohexanebis(methylamine) is readily separated from the product by fractionation under reduced pressure. Only monoethoxylated compound remains and can be used as such or further purified by distillation at reduced pressure.

Workup

  1. additionIn a 20 minute period, there is introduced with good agitation and beneath the liquid surface a total of 1.1 gm
  2. temperatureThe reaction temperature is maintained at 45°-50° C. for an additional one-half hour
  3. customThe methyl alcohol is removed by distillation at atmospheric pressure
  4. customexcess 1,4-cyclohexanebis(methylamine) is readily separated from the product by fractionation under reduced pressure
  5. distillationfurther purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-af4c67f2f2a14770b99bf9833a8bce0d
Source dataset
uspto-grants-1977_07
Patent number
US04035174

Linked notes

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