Reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.C1C=CC2S(=O)(=O)OC(C3C=C(Br)C(O)=C(Br)C=3)(C3C=C(Br)C(O)=C(Br)C=3)C=2C=1.Cl.Cl[C:40]([O:42][CH2:43][CH3:44])=[O:41].[OH-].[Na+].N1CCNCC1>O>[CH2:43]([O:42][C:40]([N:6]1[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]1)=[O:41])[CH3:44]Participants
Procedure
To a solution of 50 grams of cis-2,6-dimethylpiperazine in 130 ml. of water and containing bromphenol blue as indicator is added, with stirring and cooling, a solution of 100 ml. of concentrated hydrochloric acid in 500 ml. of water until the bromphenol blue just turns yellow. Then, 47.7 grams of ethyl chloroformate is introduced in 5 ml. portions of rapid, dropwise addition with stirring. After each 5 ml. addition, aqueous 25% sodium hydroxide solution is added dropwise until the indicator turns green. The addition of reactants is continued until thin layer chromatography shows that all of the piperazine has reacted. The reaction mixture is then made alkaline with aqueous 50% sodium hydroxide solution and then extracted with ethyl ether. The combined ether extracts are dried over anhydrous sodium sulfate and then chromatographed to give 1-ethoxycarbonyl-cis-3,5-dimethylpiperazine.
Workup
- additionis added
- temperaturecooling
- additionportions of rapid, dropwise addition
- stirringwith stirring
- additionis added dropwise until the indicator
- additionThe addition of reactants
- customhas reacted
- extractionextracted with ethyl ether
- dry with materialThe combined ether extracts are dried over anhydrous sodium sulfate
- customchromatographed
Sources & evidence
- ORD record
- ord-a7f3df1cf4454db2a03095ad2d28bd80
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04036828
Linked notes
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