Dimethylamine → 2-hydroxy-N,N-dimethylhexanamide

HRID 875293Notes

Reaction equation

HRID 875293 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH3:11])[C:3](OCC)=[O:4].C[O-].[Na+].CO.[CH3:17][NH:18][CH3:19].P(=O)(O)(O)O>>[OH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([N:18]([CH3:19])[CH3:17])=[O:4]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 887Methanol2×HCID 1004Phosphoric AcidHCID 103589Hexanoic acid, 2-hydroxy-, ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 866742372-hydroxy-N,N-dimethylhexanamideYield 81%

Procedure

In a three-neck flask, at 20° C. and under an inert atmosphere, are mixed ethyl 2-hydroxycaproate (24.24 g; 150 mmol) and sodium methylate in solution in methanol (25% w/w) (1.6 g; 7 mmol). To this mixture, is added dimethylamine in solution in methanol (50% w/w) (26.75 g; 297 mmol) within 30 minutes. The temperature of this mixture is brought to 40° C. and maintained for 3 hours. After the return of the temperature of this reaction mixture to 20° C., orthophosphoric 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 of 98%, i.e. a yield of 81%.

Workup

  1. customis brought to 40° C.
  2. temperaturemaintained for 3 hours
  3. customis obtained
  4. customThe salts formed
  5. customare removed by filtration
  6. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-223a18b945c34e038e57adfa83109e98
Source dataset
uspto-grants-2015_03
Patent number
US08981150B2

Reaction notes

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