Triethylamine → HCID 23069771, compound
Reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.FC(F)(F)S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH2:3][CH2:2]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
Benzyl 1-piperazinecarboxylate (2.0 g, 9.08 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.5 g, 10.8 mmol) and triethylamine (1.9 mL, 13.8 mmol) were dissolved in 50 mL of tetrahydrofuran, and the reaction mixture was stirred at 60° C. for two hours. After cooling to room temperature, the reaction mixture was mixed with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate twice. The combined organic layers were sequentially washed with water and brine in this order. The mixture was dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Fuji Silysia, NH Silica gel; ethyl acetate:hexane-50:50) to give 4-(2,2,2-trifluoroethyl)piperazin-1-carboxylic acid benzyl ester (3.1 g) as a colorless oil.
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with ethyl acetate twice
- washThe combined organic layers were sequentially washed with water and brine in this order
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- customevaporated
- customThe resulting residue was purified by silica gel column chromatography (Fuji Silysia, NH Silica gel; ethyl acetate:hexane-50:50)
Sources & evidence
- ORD record
- ord-3724c626394a436a89912d4b0c185709
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07619100B2
Reaction notes
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