Some tips on 1-Boc-2-oxopiperazine

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.889958-14-9,1-Boc-2-oxopiperazine,as a common compound, the synthetic route is as follows.

EXAMPLE 23 t-Butyl 3-oxo-2-phenylthio-1-piperazinecarboxylate (23) To a solution of dry diisopropylamine (0.31 ml, 2.2 mmole) and dry THF (2 ml) at 0 C. under argon is added dropwise, a hexane solution of n-butyllithium (0.90 ml, 2.2 mmole). After 1/2 hour of stirring a solution of 2 (0.200 g, 1.00 mmole) in 5 ml of dry THF is added dropwise and stirring continued for 3 hours. A solution of diphenyldisulfide (0.240 g, 1.10 mmole) in dry THF was added dropwise and the mixture is stirred for 1 hour at 0 C. before being allowed to warm to room temperature. Stirring is continued overnight and the reaction is quenched into ether/water and the aqueous phase extracted twice with ether. The ethereal extracts are washed with brine and dried over Na2 SO4, and the solvent is evaporated. The resulting yellow oil was chromatographed with 50% ethylacetate/chloroform and triturated with ether to afford 0.180 g (59%) of colorless solid 23. M.p. 138- 140 C. Alternatively, the phenyl ester of benzenesulfonothioic acid may be employed in place of diphenyldisulfide to prepare 23., 889958-14-9

The synthetic route of 889958-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Richardson-Merrell Inc.; US4341698; (1982); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of 889958-14-9

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.889958-14-9,1-Boc-2-oxopiperazine,as a common compound, the synthetic route is as follows.

EXAMPLE 25 t-Butyl 3-oxo-2-benzylidenyl-1-piperazinecarboxylate (25) To a solution of diisopropylamine (0.31 ml, 2.2 mmole) and dry THF (2 ml) at 0 C. under argon is added dropwise a hexane solution of n-butyllithium (0.90 ml, 2.2 mmole). After 1/2 hour, a solution of 2 (0.200 g, 1.00 mmole) in dry THF is added dropwise and stirred at 0 C. for 3 hours, and benzaldehyde (0.11 ml, 1.1 mmole) added dropwise. The reaction is stirred for 1 hour, the cooling bath is removed and the reaction stirred for an additional 2 hours. Acetyl chloride (0.078 ml, 1.1 mmole) was added and the mixture stirred overnight, quenched into ether/water, and purified as described in Example 23. Chromatography on silica gel with 10% methanol/chloroform yields colorless solid 25. M.p. 191-193 C.

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Reference£º
Patent; Richardson-Merrell Inc.; US4341698; (1982); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 889958-14-9

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889958-14-9, EXAMPLE 35 t-Butyl 3-Oxo-2-(alpha-hydroxy-4-fluorobenzyl)-1-piperazine carboxylate (35) To a solution of diisopropylamine (3.1 ml, 22 mmole) and dry THF (5 ml) at 0 C. under argon is added dropwise a hexane solution of n-butyllithium (13.8 ml, 22 mmole). After 3/4 hour, a solution of 2 (2.0 g, 10 mmole) in 75 ml of dry THF is added dropwise and stirred at 0 C. for 3 hours and 4-fluoro-benzaldehyde (13.6 g, 11 mmole) added dropwise. The reaction mixture was stirred at room temperature for 68 hours, poured into water, and extracted into ether. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure, and the residue recrystallized from ethanol to give 35. M.p. 219 C. (dec.)

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Reference£º
Patent; Richardson-Merrell Inc.; US4341698; (1982); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.889958-14-9,1-Boc-2-oxopiperazine,as a common compound, the synthetic route is as follows.,889958-14-9

Methyl 4-(t-Butoxycarbonyl)-2-oxo-3-(4-benzyloxybenzyl)-1-piperazineacetate (4a) To a solution of dry diisopropylamine (0.31 ml, 2.2 mmole) in 2 ml of dry THF at 0 C. under argon was added dropwise via syringe a hexane solution of n-butyllithium (0.9 ml, 2.2 mmole). After about 1/2 hour, a solution of t-boc piperazinone (2) (0.200 g, 1.00 mmole) in 5 ml of THF was added dropwise via syringe. The resulting solution was allowed to metallate at 0 C. for 3 hours after which a solution of 4-benzyloxybenzyl chloride (0.256 g, 1.1 mmole) in 2 ml of dry THF was added and the resulting solution stirred at 0 C. for one hour, allowed to warm to room temperature and stirred overnight. Methyl alpha-bromoacetate (0.095 ml, 1.1 mmole) was added to the solution via syringe and the solution stirred overnight at room temperature and quenched into ethyl ether/water. The aqueous phase was extracted twice with ether and the combined ethereal extracts washed with saturated sodium chloride solution and dried over Na2 SO4. The solvent was evaporated and the resulting yellow oil chromatographed with 20% ethylacetate/chloroform to yield 4a, as an oil, which crystallized upon standing. M.p. 84-87 C.

889958-14-9 1-Boc-2-oxopiperazine 21868412, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Richardson-Merrell Inc.; US4341698; (1982); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics