Triethylamine → N-Methoxy-N-methyl-4-oxocyclohexanecarboxamide

HRID 626178Notes

Reaction equation

HRID 626178 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.C(Cl)(=O)C(Cl)=O.CCN(CC)CC.Cl.[CH3:25][NH:26][O:27][CH3:28]>C(Cl)Cl.O>[CH3:28][O:27][N:26]([CH3:25])[C:8]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]1)=[O:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1927304-Oxocyclohexanecarboxylic acid

Product 1

HCID 89657356N-Methoxy-N-methyl-4-oxocyclohexanecarboxamideYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-oxocyclohexanecarboxylic acid (4.2 g, 0.0293 mol) in CH2Cl2 (20 mL) was added oxalyl chloride (5.2 g, 0.44 mol) slowly, stirred at room temperature for 1 hour and concentrated, then 20 mL CH2Cl2 was added, followed by addition of Et3N (9 g, 0.116 mol) and N,O-dimethylhydroxylamine hydrochloride (3.5 g, 0.0359 mol). The reaction mixture was stirred for 2 hours, and then 100 mL water was added. The mixture was extracted with ethyl acetate. The extract was concentrated and purified by column chromatography to give the desired product (2.1 g, 39% yield).

Workup

  1. concentrationconcentrated
  2. addition20 mL CH2Cl2 was added
  3. stirringThe reaction mixture was stirred for 2 hours
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-0c683d434d2342d7a29b14e05751a56a
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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