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

HRID 1834494Notes

Reaction equation

HRID 1834494 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° C.-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° C.-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 remained and could 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° C.-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-84e8b38b856b40f28789f54fa1e2a910
Source dataset
uspto-grants-1978_01
Patent number
US04070400

Reaction notes

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