Triethylamine → 1-(4-aminophenyl)-piperidin-2-one O-methyl oxime

HRID 350667Notes

Reaction equation

HRID 350667 reaction equation
C(N(CC)CC)C.[I-].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=2SC)=[CH:12][CH:11]=1.[Cl-].[CH3:25][O:26][NH3+:27]>C(O)C>[CH3:25][O:26][N:27]=[C:21]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:13]1[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 121144091-(4-Aminophenyl)-6-methylsulfanyl-2,3,4,5-tetrahydropyridinium iodide

Product 1

HCID 854347211-(4-aminophenyl)-piperidin-2-one O-methyl oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.5 ml (25 mmol) of triethylamine are added to a solution of 2.68 g (12.1 mmol) of 1-(4-aminophenyl)-6-methylsulfanyl-2,3,4,5-tetrahydro-pyridinium iodide and 1.01 g (12.1 mmol) of O-methylhydroxylammonium chloride in 30 ml of ethanol, and the mixture is stirred at room temperature for 20 hours. The reaction mixture is evaporated and taken up in water, and the resultant precipitate is filtered off, giving 1-(4-aminophenyl)-piperidin-2-one O-methyl oxime as a colourless solid; ESI 220.

Workup

  1. customThe reaction mixture is evaporated
  2. filtrationthe resultant precipitate is filtered off

Sources & evidence

ORD record
ord-37089ccdbcd543a9a0a4a66fd74b8f90
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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