Methanol → HCID 12143940, compound

HRID 2113779Notes

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-4d7fbf78060f446697e2fe0821d2a78c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432283B2

Reaction notes

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