Ammonia → 1-Amino-3-({[4-(aminomethyl)cyclohexyl]methyl}amino)propan-2-ol

HRID 2071878Notes

Reaction equation

HRID 2071878 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]([CH:13]1[O:15][CH2:14]1)Cl.[OH-].[NH4+:17].C(Cl)C(O)C.N>CO>[NH2:17][CH2:11][CH:13]([OH:15])[CH2:14][NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][NH2:10])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 7835EpichlorohydrinHCID 14923Ammonium HydroxideHCID 173541,4-CyclohexanedimethanamineHCID 313701-Chloro-2-propanol

Product 1

HCID 203734301-Amino-3-({[4-(aminomethyl)cyclohexyl]methyl}amino)propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
20 °C

Procedure

1,4-Cyclohexanebis(methylamine) (14.2 g., 0.1 mole) is dissolved in 50 ml. of anhydrous methyl alcohol and the solution cooled to +5° C. in an ice bath. Epichlorohydrin (9.3 g., 0.1 mole) is added in a 2-minute period and the temperature maintained at +5° C. for 2 hours; reaction is allowed to continue at 10°-15° C. until thin layer chromatography of an aliquot (silica gel plate with development using a solution of 1 volume concentrated aqueous ammonium hydroxide in 4 volumes of methyl alcohol) indicated nearly complete conversion of the starting diamine to the propylene chlorohydrin. The solution is then added to 100 ml. of dry methyl alcohol previously saturated at 0° C. with dry ammonia gas by continuous dropwise flow at +5° C. with good agitation and external cooling. After stirring 2 hours at +5° C., it is allowed to warm to 20° C. and mixed overnight. The reaction is competed by heating at 45°-55° C. for 6 hours. The solvent and ammonia was removed by stripping and the product purified using fractional distillation under reduced pressure.

Workup

  1. temperaturethe temperature maintained at +5° C. for 2 hours
  2. customreaction
  3. customto continue at 10°-15° C. until thin layer chromatography of an aliquot
  4. additionThe solution is then added to 100 ml
  5. custompreviously saturated at 0° C.
  6. customat +5° C.
  7. additionmixed overnight
  8. temperatureby heating at 45°-55° C. for 6 hours
  9. customThe solvent and ammonia was removed
  10. customthe product purified
  11. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-c6ea3f60e7444979a4763b1e39a658b2
Source dataset
uspto-grants-1977_09
Patent number
US04049417

Reaction notes

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