Methanol → HCID 12143940, compound

HRID 916206Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[S:16].[C:17](=O)([O:20]C)[O:18][CH3:19].[H-].[Na+].[CH3:25]O>O1CCOCC1>[CH3:19][O:18][C:17]([C:12]1[CH2:13][CH2:14][CH2:15][N:10]([C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[Cl:1])[C:11]=1[S:16][CH3:25])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

1-(2-Chloro-4,6-dimethylphenyl)piperidine-2-thione (5.11 g), dimethyl carbonate (17.0 mL), sodium hydride (3.7 g of a 60% dispersion in mineral oil), and methanol (0.5 mL) were combined in 100 mL of dioxane and the mixture was stirred in a 120° C. oil bath for 4 h. After the reaction had cooled to room temperature, it was quenched by the addition of aqueous ammonium chloride, diluted with water and washed twice with ethyl acetate. After drying over magnesium sulfate, the ethyl acetate was concentrated and the residue chromatographed on silica gel using an acetone/hexane gradient to provide 5.00 g 1-(2-chloro-4,6-dimethylphenyl)-2-methylsulfanyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester, mp 85.3-87.6° C.

Workup

temperatureAfter the reaction had cooled to room temperature
customit was quenched by the addition of aqueous ammonium chloride
additiondiluted with water
washwashed twice with ethyl acetate
dry with materialAfter drying over magnesium sulfate
concentrationthe ethyl acetate was concentrated
customthe residue chromatographed on silica gel using an acetone/hexane gradient

Sources & evidence

ORD record: ord-44d7c6f454644111bea41f3dcad6a7f9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268146B2

Reaction notes

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