Piperidine → HCID 67288919, compound
Reaction equation
[F:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>ClCCl>[F:1][C:2]1[C:3]([C:4]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:6])=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
162 g (1.47 mol, 1.05 eq) of N-methylmorphorine was added to the mixed solution of 278 g (1.4 mol, 1.0 eq) of 2-fluoro-3-(methoxycarbonyl)benzoic acid obtained from the Step 2 and 2.7 l of dichloromethane, and then stirred for 30 minutes at 0° C. 191 ml (1.47 mol, 1.05 eq) of isobutyl chloromate was slowly added, and then stirred for 1 hour at 0° C. 139 ml (1.4 mol, 1.0 eq) of piperidine was slowly added, and then stirred for 1 hour at a room temperature. After completing the reaction, the reaction solution was washed with 560 ml of a saturated sodium bicarbonate aqueous solution, 560 ml of a saturated ammonium chloride aqueous solution, and 1 l of distilled water in order. A obtained organic layer was dehydrated with magnesium sulfate anhydrous, filtered, and then concentrated under reduced pressure to obtain 371 g of methyl 2-fluoro-3-(piperidine-1-carbonyl)benzoate in a red-yellow oil phase
Workup
- addition191 ml (1.47 mol, 1.05 eq) of isobutyl chloromate was slowly added
- stirringstirred for 1 hour at 0° C
- stirringstirred for 1 hour at a room temperature
- customthe reaction
- washthe reaction solution was washed with 560 ml of a saturated sodium bicarbonate aqueous solution, 560 ml of a saturated ammonium chloride aqueous solution, and 1 l of distilled water in order
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2d763c3b9b2b42c7b73fb25a6b910cea
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742160B2
Reaction notes
Loading…