Methanol → Methyl 3-[(4-methyl-1-piperidinyl)sulfonyl]benzoate

HRID 877628Notes

Reaction equation

HRID 877628 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=[O:15])(=[O:10])=[O:9])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH3:25]O>>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([O:16][CH3:25])=[O:15])(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2842864HCID 2842864, compound

Product 1

HCID 793741Methyl 3-[(4-methyl-1-piperidinyl)sulfonyl]benzoateYield 75%

Procedure

3-((4-methylpiperidin-1-yl)sulfonyl)benzoic acid (120 mg, 0.424 mmol) was refluxed in the presence of con. Sulfuric acid (2.74 mg, 0.021 mmol) in methanol at 70° C. for overnight. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by flash chromatography afforded the methyl 3-((4-methylpiperidin-1-yl)sulfonyl)benzoate (100 mg, 0.319 mmol, 75% yield). 1H NMR (CDCl3, 400 MHz): δ 8.39 (m, 1H), 8.25 (m, 1H), 7.94 (m, 1H), 7.62 (t, 1H, J=7.6 Hz), 3.95 (s, 3H), 3.77 (m, 2H), 2.25 (m, 2H), 1.67 (m, 2H), 1.29 (m, 3H), 0.90 (d, 3H, J=4.8 Hz). ESI-MS: 298.1[M+H]+

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by flash chromatography

Sources & evidence

ORD record
ord-7f3b7ff11f19471ca9de865c523620c7
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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