4-Methylmorpholine → HCID 15682564, compound

HRID 1590002Notes

Reaction equation

HRID 1590002 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.CN(C1C=CC=CN=1)C.[CH3:23][O:24][C:25]([C:27]1[C:28]([CH3:35])=[N:29][O:30][C:31]=1[C:32](O)=[O:33])=[O:26]>ClCCl.C(OCC)(=O)C>[N:1]1([C:32]([C:31]2[O:30][N:29]=[C:28]([CH3:35])[C:27]=2[C:25]([O:24][CH3:23])=[O:26])=[O:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 218852-DimethylaminopyridineHCID 5325770HCID 5325770, compound

Product 1

HCID 15682564HCID 15682564, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

At -5° C., 3.0 g (35.1 mmol) of piperidine, 10.1 g (100.0 mmol) of methylmorpholine, 1.1 g (9 mmol) of dimethylaminopyridine and 22.9 g of a 50% strength solution of propanephosphonic anhydride in dichloromethane (36.0 mmol) were added one after the other to 5.0 g (27.0 mmol) of 4-methoxycarbonyl-3-methyl-isoxazole-5-carboxylic acid in 100 ml of dichloromethane, and the mixture was stirred for 12 hours at room temperature. The solvent was stripped off under reduced pressure, and the residue was taken up in 200 ml of ethyl acetate and extracted twice with saturated sodium bicarbonate solution and once with 5% strength citric acid solution and once with saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and the solvent was stripped off under reduced pressure. Yield: 90%, 1H-NMR (250 MHz; CDCl3): δ=1.65 ppm (m; 6H), 2.49 ppm (s; 3H), 3.18 ppm (m; 2H), 3.73 ppm (m; 2H), 3.87 ppm (s; 3H).

Workup

  1. extractionextracted twice with saturated sodium bicarbonate solution and once with 5% strength citric acid solution and once with saturated sodium chloride solution
  2. dry with materialThe organic phase was dried over magnesium sulfate

Sources & evidence

ORD record
ord-9b27c93776304a368c765f3afabf4a83
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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