Triethylamine → 4-Methylene-8-(4-methylpiperazine-1-ylcarbonyl)-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[CH2:11]=[C:12]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[O:15][C:14](=[O:22])[N:13]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:11]=[C:12]1[C:16]2([CH2:21][CH2:20][N:19]([C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:9])[CH2:18][CH2:17]2)[O:15][C:14](=[O:22])[N:13]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of 3.9 g of 4-methylpiperazin-1-yl-carbonyl chloride in 5 ml of chloroform is dropwise added at a temperature between 0° and 5° C. to a solution containing 4.9 g of 4-methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane and 7.4 ml of triethylamine in 74 ml of chloroform under stirring. Thereafter, the reaction mixture is stirred at room temperature for an additional 30 minutes. After termination of the reaction the chloroform phase is washed to chloride-free with water, dried over anhydrous sodium sulfate, then the solvent is evaporated under reduced pressure. After recrystallization of the crude product obtained from ethanol under clarifying by activated carbon the title compound is obtained in 83% yield, m.p.: 198°-199° C.
Workup
- stirringThereafter, the reaction mixture is stirred at room temperature for an additional 30 minutes
- washis washed to chloride-free with water
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent is evaporated under reduced pressure
- customAfter recrystallization of the crude product
Sources & evidence
- ORD record
- ord-27ad59348f4d4bea85ceaa1950fb9fee
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05157038
Reaction notes
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