Dimethylamine → 2-hydroxy-N,N-dimethylhexanamide

HRID 875294Notes

Reaction equation

HRID 875294 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][CH3:10])[C:3]([O:5]CC)=O.[CH3:11][O-].[Na+].CO.[CH3:16][NH:17][CH3:18]>>[OH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([N:17]([CH3:18])[CH3:16])=[O:5]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 887Methanol2×HCID 96120Ethyl 2-hydroxypentanoateHCID 10942334Sodium Methoxide

Product 1

HCID 866742372-hydroxy-N,N-dimethylhexanamideYield 80%

Procedure

In a three-neck flask, at 20° C. and under an inert atmosphere, are mixed ethyl 2-hydroxyvalerate (31 g; 210 mmol) and sodium methylate in solution in methanol (25% w/w) (2.2 g; 10 mmol). To this mixture, is added dimethylamine in solution in methanol (50% w/w) (37.1 g; 411 mmol) within 30 minutes. The temperature of this mixture is brought to 40° C. and maintained for 3 hours. After return of the temperature of the reaction mixture to 20° C., orthophosphonic acid is added until a pH of 5 is obtained. The salts formed are removed by filtration and the solvents are removed under reduced pressure. 2-hydroxy-N,N-dimethylhexanamide is then obtained with a purity <98% i.e. a yield of 80%.

Workup

  1. customis brought to 40° C.
  2. temperaturemaintained for 3 hours
  3. additionAfter return of the temperature of the reaction mixture to 20° C., orthophosphonic acid is added until a pH of 5
  4. customis obtained
  5. customThe salts formed
  6. customare removed by filtration
  7. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-113ae9b257e5427ea54aceea914c378a
Source dataset
uspto-grants-2015_03
Patent number
US08981150B2

Reaction notes

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