HCID 20192358, compound → HCID 178457328, compound

HRID 2118990Notes

Reaction equation

HRID 2118990 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:9]([C:11]2[C:12]([CH2:17][CH3:18])=[N:13][O:14][C:15]=2[CH3:16])=[O:10])[CH:5]=[CH:6][CH:7]=1>[Pd].C(O)C>[C:15]([C:11](=[C:12]([NH2:13])[CH2:17][CH3:18])[C:9]([N:8]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[O:10])(=[O:14])[CH3:16]

Participants

4

Reactant 1

HCID 20192358HCID 20192358, compound

Product 1

HCID 178457328HCID 178457328, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 15.3 grams (0.048 mole) of N-(m-fluorophenyl)-N-(2-dimethylaminoethyl)-3-ethyl-5-methyl-4-isoxazole carboxamide and 1.5 grams of 10% palladium on carbon in 120 ml. of ethanol is hydrogenated at 50 psi at room temperature overnight. The catalyst is then removed by filtration and the solvent evaporated in vacuo. The residue is crystallized from ether; petroleum ether (1:1) to give 2-acetyl-3-amino-N-(2-dimethylaminoethyl)-N-(m-fluorophenyl)-2-pentenamide (m.p. 96°-97° C.).

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe solvent evaporated in vacuo
  3. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-0a6dbca792e14ee8a341a394cd4762e0
Source dataset
uspto-grants-1987_07
Patent number
US04681898

Reaction notes

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