N-Cyclohexyl-1,3-propanediamine → N-(3'-Cyclohexylaminopropyl)-aspartic acid-4-methyl ester

HRID 894729

Reaction equation

HRID 894729 reaction equation
[CH3:1][O:2][C:3](=[O:9])/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].[CH:10]1([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:9])[CH2:4][C@@H:5]([C:6]([OH:8])=[O:7])[NH:20][CH2:19][CH2:18][CH2:17][NH:16][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 18718N-Cyclohexyl-1,3-propanediamineHCID 5354456Monomethyl maleate

Product 1

HCID 22817118N-(3'-Cyclohexylaminopropyl)-aspartic acid-4-methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

356 g (3.4 mols+14% excess) of maleic acid monomethyl ester are placed into a glass flask provided with stirrer, thermometer, condenser and dropping funnel, and, with vigorous stirring and ice-water cooling, 480 ml of triethylamine are added dropwise at 5°-8° C. internal temperature within 2 hours. 372.6 g (2.4 mols) of 3-cyclohexylaminopropylamine are then quickly introduced; the exothermic reaction is subsequently allowed to subside, and the reaction mixture is heated within 30 minutes to 85° C., in the course of which the reaction product crystallises out. After the reaction has finished, the temperature is lowered to room temperature; the product is mixed with 1100 ml of acetone and is filtered off; the filter residue is again mixed with 900 ml of acetone, and the suspension is filtered; the filter residue is then washed with acetone, and the product is dried at 60° C. and 53.2 mbars. The yield is 555.4 g (87.2% of theory) of a white crystalline aspartic acid derivative, which decomposes at 163° C.

Workup

  1. customprovided with stirrer
  2. customthermometer, condenser and dropping
  3. customthe exothermic reaction
  4. temperaturethe reaction mixture is heated within 30 minutes to 85° C., in the course of which the reaction product
  5. customcrystallises out
  6. customis lowered to room temperature
  7. additionthe product is mixed with 1100 ml of acetone
  8. filtrationis filtered off
  9. additionthe filter residue is again mixed with 900 ml of acetone
  10. filtrationthe suspension is filtered
  11. washthe filter residue is then washed with acetone
  12. customthe product is dried at 60° C.
  13. customdecomposes at 163° C.

Sources & evidence

ORD record
ord-58a3ef1e204540818488d31ff05e6679
Source dataset
uspto-grants-1981_08
Patent number
US04284755

Linked notes

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