Water → N-Methoxy-N-methylheptanamide

HRID 378238Notes

Reaction equation

HRID 378238 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][NH:10][O:11][CH3:12].[C:13](Cl)(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O>C(Cl)Cl>[CH3:9][N:10]([O:11][CH3:12])[C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 17313Heptanoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 13642088N-Methoxy-N-methylheptanamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (19.6 g, 194 mmol) was added dropwise to a suspension of N,O-dimethylhydroxylamine hydrochloride (6.93 g, 71 mmol) in anhydrous CH2Cl2 at 0° C. Heptanoylchloride (9.60 g, 65 mmol) was then added dropwise and the reaction was stirred 1 hour. The crude product mixture was poured into water and the separated aqueous phase was extracted with CH2Cl2. The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10 g (89%) N-methyl-N-methoxyheptanamide as a yellow oil.

Workup

  1. extractionthe separated aqueous phase was extracted with CH2Cl2
  2. washThe combined organic layers was washed with aq. HCl, sat. NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7df0f8f295884cce91caac90f648e6e1
Source dataset
uspto-grants-2000_02
Patent number
US06030969

Reaction notes

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