ChemicalBook CAS DataBase List 4-Benzylpiperidine

4-Benzylpiperidine synthesis

8synthesis methods

Product Name:4-Benzylpiperidine
CAS Number:31252-42-3
Molecular formula:C12H17N
Molecular Weight:175.27

4-Benzylpiperidine can be prepared by reacting 4-cyanopyridine with toluene. Catalytic hydrogenation of the pyridine ring then completes the synthesis.

4-benzyl-1-[(4-methylphenyl)sulfonyl]piperidine

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Yield:31252-42-3 92%

Steps:

Next, the progress made so far in investigating the functional group tolerance is presented below. The tosyl derivatives of amines were made by reacting secondary amines with para toluene sulfonyl chloride (TsCl) in Et₃N. It was demonstrated that detosylation works well for tosyl derivatives of dicyclohexyl amine (abbreviated Cy₂NTs in table above), pyrrolidine, morpholine, BMEA (bis(2-methoxy-ethyl) amine), phenyl methyl amine, 4-benzylpipiridine, benzyl methyl amine. Similar results are also expected to be achieved for additional tosyl amines such as HMDS etc.Table 4 below presents studies that map out the reaction's functional group tolerance. TABLE 4 The Reaction's Functional Group Tolerance (Not Fully Optimized) % Yield % Yield (Sequential (One-Pot/Solid Reactant Product Protonation) Acid) 1. 92 82 2. 82 83 3. 85 75 4. 85 86 5. 74 75 6. 83 80

References:

US2009/306391,2009,A1 Location in patent:Page/Page column 7