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ChemicalBook CAS DataBase List 1-Boc-4-cyanopiperidine
91419-52-2

1-Boc-4-cyanopiperidine synthesis

11synthesis methods
N-Boc-4- cyanopiperidine is an organic heterocyclic compound, which can be used as pharmaceutical intermediates. The synthesis of 1-Boc-4-cyanopiperidine is through the dehydration of oximes and amides to nitriles. The solution of the aldoxime and XtalFluor-E8 is mixed to extract with CH2Cl2 (2 × 10 mL), The combined organic layers were washed, dried, and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required.
137076-22-3 Synthesis
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde

137076-22-3
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$5.00/1g

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Yield:91419-52-2 73%

Reaction Conditions:

with potassium hexafluorophosphate;tert.-butylnitrite;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;oxygen;1,1,1,3,3,3-hexamethyl-disilazane in acetonitrile at 30; for 8 h;

Steps:

23 Example 23: Preparation of N-Boc-4-piperidinecarbonitrile (Formula (2-8))
In a 100-ml flask, 30 mL of acetonitrile, 10 mmol of HMDS, 0.4 mmol of TEMPO, 0.4 mmol of KPF6 and 0.6 mmol of TBN were charged. The air was replaced with oxygen. The mixture was heated to 30 ° C in a preheated water bath and 4 mmol of N-Boc-4-piperidinecarboxaldehyde (as shown in formula (1-8)) was added slowly for 8 h. The reaction mixture was stirred with sodium thiosulfate solution and extracted with ether. The organic layer was separated, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography. The mixture was stirred at a volume ratio of ethyl acetate / petroleum ether of 1: 100 The eluent containing the title compound was collected and the solvent was evaporated to give N-Boc-4-piperidinecarbonitrile in an isolation yield of 70%.; The reaction procedure was the same as in Example 20, except that the amount of acetonitrile used was 80 mL, and the isolated yield of N-Boc-4-piperidinecarbonitrile was 73%.

References:

Zhejiang University of Technology;Li, Meichao;Chen, Zhenlu;Tang, Chaojie;Mo, Weimin CN105481624, 2016, A Location in patent:Paragraph 0041; 0042

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