Methyl iodide → 1-(4-Aminophenyl)-6-methylsulfanyl-2,3,4,5-tetrahydropyridinium iodide

HRID 230730Notes

Reaction equation

HRID 230730 reaction equation
[I:1][CH3:2].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[S:16])=[CH:6][CH:5]=1>CC(C)=O>[I-:1].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[S:16][CH3:2])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 121144081-(4-Aminophenyl)piperidine-2-thione

Product 1

HCID 121144091-(4-Aminophenyl)-6-methylsulfanyl-2,3,4,5-tetrahydropyridinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.2 1.25 ml (20.0 mmol) of iodomethane are added to a solution of 3.74 g (18.1 mmol) of 1-(4-aminophenyl)piperidine-2-thione in 30 ml of acetone, and the mixture is stirred at room temperature for 48 hours. The reaction mixture is evaporated, giving 1-(4-aminophenyl)-6-methylsulfanyl-2,3,4,5-tetrahydropyridinium iodide as a brownish solid; ESI 221. 2.3 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)peperidin-2-one O-methyl oxime as a colourless solid; ESI 220.

Workup

  1. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-d39946aee42043c0a46720b816df1429
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Reaction notes

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