1-Dodecanol → Dodecyl N,N-dimethylalaninate

HRID 2227562Notes

Reaction equation

HRID 2227562 reaction equation
[CH3:1][N:2]([CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].[CH2:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CC.C[O-].[Na+]>C(O)C>[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:9][CH2:8][O:7][C:5]([CH:4]([N:2]([CH3:3])[CH3:1])[CH3:10])=[O:6]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 10942334Sodium MethoxideHCID 13010786HCID 13010786, compound

Product 1

HCID 3025823Dodecyl N,N-dimethylalaninate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ethyl 2-(N,N-dimethylamino)-propionate is preferably refluxed for about 2 hours in the presence of 10 percent stoichiometric excess 1-dodecanol and a catalytic amount of sodium methoxide (predissolved in toluene). During this process, the ethanol formed is removed from the reaction medium by azeotropic distillation. Following the reaction phase, the solids of the remaining mixture are filtered off, resulting in a DDAIP filtrate.

Workup

  1. customis removed from the reaction medium by azeotropic distillation
  2. filtrationthe solids of the remaining mixture are filtered off

Sources & evidence

ORD record
ord-2b08247520fe4053914436398c6476ff
Source dataset
uspto-grants-2002_07
Patent number
US06414028B1

Reaction notes

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