tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Product Name
- tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- CAS No.
- 692058-21-2
- Chemical Name
- tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Synonyms
- 1-Boc-4-(2,2,2-trifluoroethyl)piperazine;tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate;1-Piperazinecarboxylic acid, 4-(2,2,2-trifluoroethyl)-, 1,1-dimethylethyl ester
- CBNumber
- CB82719555
- Molecular Formula
- C11H19F3N2O2
- Formula Weight
- 268.28
- MOL File
- 692058-21-2.mol
tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate Property
- storage temp.
- 2-8°C
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- T135815
- Product name
- tert-Butyl4-(2,2,2-Trifluoroethyl)piperazine-1-carboxylate
- Packaging
- 500mg
- Price
- $200
- Updated
- 2021/12/16
- Product number
- FB142405
- Product name
- tert-Butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Packaging
- 500mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- FB142405
- Product name
- tert-Butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Packaging
- 2g
- Price
- $162
- Updated
- 2021/12/16
- Product number
- 9377CW
- Product name
- Tert-butyl4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Packaging
- 10g
- Price
- $319
- Updated
- 2021/12/16
- Product number
- FB142405
- Product name
- tert-Butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate
- Packaging
- 5G
- Price
- $324
- Updated
- 2021/12/16
tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate Chemical Properties,Usage,Production
Synthesis
77278-37-6
692058-21-2
General procedure: tert-butyl-1-piperazinecarboxylate (1.00 g, 5.37 mmol) and pyridine (0.868 mL, 10.7 mmol) were dissolved in dichloromethane (27 mL) and the mixture was cooled to 0 °C. Subsequently, trifluoroacetic anhydride (0.910 mL, 6.44 mmol) was slowly added dropwise and the reaction mixture was gradually warmed up to room temperature with continuous stirring for 1 hour. Upon completion of the reaction, the reaction solution was diluted with ethyl acetate (150 mL) and washed sequentially with aqueous potassium bisulfate (2 x 50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate (1.50 g, 99%) as an oil, which solidified on standing. Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate (0.908 g, 3.22 mmol) was dissolved in tetrahydrofuran (24 mL), borane-tetrahydrofuran complex (8 mmol) was added, and the reaction mixture was heated and refluxed for 2 hours. After cooling, 2N hydrochloric acid (4 mL) was carefully added and stirred until gas release ceased, followed by dilution with ethyl acetate (200 mL). 0.2 M aqueous sodium hydroxide (75 mL) was added and after partitioning, the organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (eluent: 20% hexane solution of ethyl acetate) to give tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate (0.627 g, 73%) as a white solid. Tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate (0.736 g, 2.74 mmol) was dissolved in dioxane (5 mL), a 4.0 M hydrochloric acid solution of dioxane (10 mL) was added, and the reaction was stirred until thin-layer chromatography analysis showed that the reaction was complete (about 3 hours). The volatiles were evaporated under reduced pressure and the residue was dried under vacuum to give 1-(2,2,2-trifluoroethyl)piperazine (0.631 g, 95%) as a white solid.
References
[1] Patent: WO2005/110996, 2005, A1. Location in patent: Page/Page column 45-46
[2] Patent: CN106187838, 2016, A. Location in patent: Paragraph 0437; 0438; 0439
[3] Patent: WO2006/46031, 2006, A1. Location in patent: Page/Page column 46-47
[4] Patent: CN105461697, 2016, A. Location in patent: Paragraph 0198; 0199
tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate Preparation Products And Raw materials
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