Potassium Iodide → 4-Methylsulfonylaminobenzoyl-1-[3-(4-pyridyl)-propyl]piperidine dihydrochloride
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]NCC2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[C:21](=O)([O-])O.[Na+].Cl.[Cl:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.[I-].[K+].C[N:40]([CH3:43])C=O>>[ClH:27].[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:21][CH2:43][N:40]2[CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:12])=[CH:19][CH:20]=1)(=[O:4])=[O:5]Participants
Reactant 5
Product 1
Conditions
- Temperature
- 85 °C
Procedure
0.295 g (0.926 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride and 0.380 g (4.52 mmol) of sodium hydrogencarbonate were suspended in 4 ml of dimethylformamide and the suspension was stirred at 85° C. for 40 min. 0.20 g (1.04 mmol) of 4-(3-chloropropyl)pyridine hydrochloride and 0.31 g (1.87 mmol) of potassium iodide were added to the suspension and the mixture was stirred at 85° C. for 1.5 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 0.288 g (66%) of the intended compound.
Workup
- stirringthe mixture was stirred at 85° C. for 1.5 h
- customThe liquid reaction mixture
- filtrationwas filtered
- concentrationthe filtrate was concentrated
- customThe obtained residue was purified
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-d7b12f61fb6940d1bc62984f20a4cd13
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04876262
Reaction notes
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