N,N-Dimethyl-1,3-propanediamine → N-(3'-Dimethylaminopropyl)-aspartic acid-4-n-butyl ester

HRID 2286013Notes

Reaction equation

HRID 2286013 reaction equation
[CH2:1]([O:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].[CH3:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17][NH2:18]>C(N(CC)CC)C>[CH3:4][CH2:3][CH2:2][CH2:1][O:5][C:6](=[O:12])[C@H:7]([CH2:8][C:9]([OH:11])=[O:10])[NH:18][CH2:17][CH2:16][CH2:15][N:14]([CH3:19])[CH3:13]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 5356726Monobutyl maleate

Product 1

HCID 86738344N-(3'-Dimethylaminopropyl)-aspartic acid-4-n-butyl esterYield 86.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In the apparatus described in Example 1, 500 ml of triethylamine are added with cooling, within 2 hours and 35 minutes, at 4°-10° C. internal temperature to 430.5 g (2.5 mols) of maleic acid-mono-n-butyl ester. There are subsequently quickly added 306.5 g (2.5 mols+20% excess) of 3-dimethylaminopropylamine, and the mixture is reacted for 30 minutes at 90°-95° C. The reaction product is processed in a manner analogous to that described in Example 1 to obtain a yield of 595 g (86.8% of theory) of a crystalline aspartic acid derivative, which melts at 154°-157.5° C.

Workup

  1. additionare added
  2. customthe mixture is reacted for 30 minutes at 90°-95° C

Sources & evidence

ORD record
ord-aea21b7460aa42a1971de9aa04474c6b
Source dataset
uspto-grants-1982_04
Patent number
US04326069

Reaction notes

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