Methanol → E-4031 dihydrochloride

HRID 892448

Reaction equation

HRID 892448 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:21][C:22]1[N:27]=[C:26]([CH:28]=[CH2:29])[CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+].CO>O>[ClH:1].[ClH:1].[CH3:21][C:22]1[N:27]=[C:26]([CH2:28][CH2:29][N:16]2[CH2:17][CH2:18][CH:13]([C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])=[CH:20][CH:19]=3)[CH2:14][CH2:15]2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 707352-Ethenyl-6-methylpyridineHCID 517045Sodium AcetateHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

Product 1

HCID 3087190E-4031 dihydrochlorideYield 150.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.254 g (0.797 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride, 0.22 g (1.88 mmol) of 6-methyl-2-vinylpyridine and 0.15 g of sodium acetate were suspended in 3 ml of a mixture of methanol and water (1:1) and the suspension was refluxed for 2 h. The liquid reaction mixture was filtered and the filtrate was concentrated. The obtained residue was purified according to silica gel column chromatography (chloroform:methanol:aqueous ammonia=96:4:0.4). The purified product was converted into its hydrochloride with ethanolic hydrogen chloride and recrystallized from ethanol to obtain 0.285 g (yield: 81%) of the intended compound.

Workup

  1. temperaturethe suspension was refluxed for 2 h
  2. customThe liquid reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe obtained residue was purified
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-50e352dc85014b8fa31de93c71520f74
Source dataset
uspto-grants-1992_06
Patent number
US05118689

Linked notes

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