Ethanolamine → N-hydroxyethyl-beta-dipropylaminopropionamide

HRID 1081995Notes

Reaction equation

HRID 1081995 reaction equation
[CH2:1]([N:4]([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][C:7]([O:9]C)=O)[CH2:2][CH3:3].C[O-].[Na+].[CH2:17]([CH2:19][NH2:20])[OH:18]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[OH:18][CH2:17][CH2:19][NH:20][C:7](=[O:9])[CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 10942334Sodium MethoxideHCID 23363412Methyl beta-dipropylaminopropionate

Product 1

HCID 54257674N-hydroxyethyl-beta-dipropylaminopropionamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 7108PhenothiazineCatalyst

Procedure

To 746 g of methyl beta-dipropylaminopropionate which was prepared in the same manner as in Example 4 were added 15.4 g of 28% methanolic solution of sodium methoxide, then 293 g (4.8 moles) of ethanolamine were added dropwise thereinto and the mixture was made to react at 70° C. for one hour. After completion of the reaction, the mixture was neutralized, desalted, 0.3 g of phenothiazine were added thereto and the low-boiling-point substances were removed by distillation to give 858 grams of N-hydroxyethyl-beta-dipropylaminopropionamide. The purity as checked by gas chromatography was 98% and the yield was 97.3%.

Workup

  1. customto react at 70° C. for one hour
  2. customAfter completion of the reaction
  3. customthe low-boiling-point substances were removed by distillation

Sources & evidence

ORD record
ord-90dcc97a434f49bb8af215354369fcef
Source dataset
uspto-grants-1996_12
Patent number
US05587515

Reaction notes

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