Tetrahydrofuran → Ethyl 2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate
Reaction equation
[OH-].[Na+].[CH3:3][CH:4]1[NH:9][CH2:8][CH2:7][N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5]1.O1CCCC1.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25]>O>[CH3:3][CH:4]1[CH2:5][N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:8][N:9]1[C:22]([O:23][CH2:24][CH3:25])=[O:26]Participants
Procedure
580 Parts of a sodium hydroxide solution 1N in water were cooled in an ice bath and then there were added 44 parts of 3-methyl-1-(phenylmethyl)piperazine and 82.8 parts of tetrahydrofuran. A solution of 27.13 parts of ethyl carbonochloridate in 103.5 parts of tetrahydrofuran was added dropwise at a temperature at about 5° C. Upon completion, stirring was continued for 4 hours in an ice bath. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 55 parts (87.8%) of ethyl 2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate as a residue (int. 36).
Workup
- extractionThe product was extracted with dichloromethane
- washThe extract was washed with water
- customdried
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
Sources & evidence
- ORD record
- ord-680202f4de0d4b8293e928706052b9c4
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04880808
Reaction notes
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