Ethyl piperidine-2-carboxylate → 1-(2-Fluoro-4-chloro-5-isopropoxycarbonylphenyl)aminocarbonyl-2-ethoxycarbonylpiperidine
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[N:15]=[C:16]=[O:17].[NH:18]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([O:11][CH:12]([CH3:13])[CH3:14])=[O:10])=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17]Participants
Procedure
5.15 g (0.02 mol) of 2-fluoro-4-chloro-5-isopropoxycarbonylphenyl isocyanate were added to a solution of 3.2 g (0.02 mol) of ethyl pipecolate dissolved in 30 ml of benzene. The mixture was stirred at a temperature of 40° to 50° C. for an hour, washed with water, dried over anhydrous sodium sulfate, and then concentrated. The resulting crystals were recrystallized from a mixed solvent of n-hexane and ethyl acetate to give 6.9 g (yield 83.2%) of 1-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)aminocarbonyl-2-ethoxycarbonylpiperidine. This compound was dissolved in 70 ml of toluene and hydrogen chloride was blown thereinto. The mixture was stirred at room temperature for three hours, washed with a saturated solution of sodium hydrogen carbonate, washed with water, dried over anhydrous sodium sulfate and then concentrated. The resulting crystals were recrystallized from a mixed solvent of toluene and ethyl acetate to give 2.6 g (yield 71.9%) of the desired product as white crystals with a melting point of 128°-129° C.
Workup
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe resulting crystals were recrystallized from a mixed solvent of n-hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-95dc7b9c0fdf4c01b5825150bb1071fa
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04531964
Reaction notes
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