Potassium Iodide → 1-(2-(2-Imidazo[1,2-a]pyridyl)ethyl]-4-(4-methylsulfonylaminobenzoyl)piperidine
Reaction equation
Cl.[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].C(=O)([O-])O.[Na+].Cl.Cl[CH2:28][CH2:29][C:30]1[N:31]=[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]2[CH:38]=1.[I-].[K+]>CN(C)C=O>[N:31]1[C:30]([CH2:29][CH2:28][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:38][N:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1.02 g (3.2 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride, 1.34 g of sodium hydrogencarbonate and 10 ml of dimethylformamide was stirred at 80° C. for 1 h. 0.48 g of 2-(2-chloroethyl)imidazo[1,2-a]pyridine hydrochloride and 0.53 g of potassium iodide were added thereto and the mixture was stirred at 80° C. for 2 h. The mixture was filtered and the filtrate was concentrated to obtain a solid residue, which was then purified according to silica gel column chromatography (chloroform:methanol:aqueous ammonia=190:9:1). The fraction of the intended compound was concentrated to obtain a solid residue, which was then recrystallized from ethyl acetate to obtain 0.25 g (yield: 18%) of the intended compound.
Workup
- stirringthe mixture was stirred at 80° C. for 2 h
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated
- customto obtain a solid residue, which
- customwas then purified
- concentrationThe fraction of the intended compound was concentrated
- customto obtain a solid residue, which
- customwas then recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-892c10a484b44b9ca0df392f8ebd7b0c
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04996215
Reaction notes
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