Formaldehyde → 1-(5-Methyl-2-furanyl)methyl-4-(4-methylsulfonylaminobenzoyl)piperidine
Reaction equation
[CH2:1]=O.[CH3:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1.[CH3:9][S:10]([NH:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)(=[O:12])=[O:11].[OH-].[Na+]>O.C(O)(=O)C>[CH3:1][C:6]1[O:5][C:4]([CH2:3][N:23]2[CH2:24][CH2:25][CH:20]([C:18](=[O:19])[C:17]3[CH:16]=[CH:15][C:14]([NH:13][S:10]([CH3:9])(=[O:11])=[O:12])=[CH:27][CH:26]=3)[CH2:21][CH2:22]2)=[CH:8][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
1.88 ml of formalin and 1.07 g of methylfuran were added to a mixture of 4.43 g (15.7 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine in free form obtained in Example 17, 1.57 ml of glacial acetic acid and 10 ml of water and the obtained mixture was stirred at 90° C. for 2 h. After cooling, the mixture was neutralized with a 20% aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous common salt solution, dried over magnesium sulfate and concentrated. The solid residue was recrystallized from ethanol/methanol to obtain 4.16 g (yield: 70%) of the intended compound.
Workup
- temperatureAfter cooling
- extractionextracted with dichloromethane
- washThe organic layer was washed with water
- dry with materiala saturated aqueous common salt solution, dried over magnesium sulfate
- concentrationconcentrated
- customThe solid residue was recrystallized from ethanol/methanol
Sources & evidence
- ORD record
- ord-2231e499fdfe46a1856c456ed4fc9f21
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05179095
Reaction notes
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