Tetrahedron

New synthesis of 3-aryl-Nn-propyl-piperidines

MY Chang, ST Chen, NC Chang

Index: Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen Tetrahedron, 2002 , vol. 58, # 18 p. 3623 - 3628

Full Text: HTML

Citation Number: 27

Abstract

The synthesis of 3-aryl-Nn-propyl-piperidines is described in six steps starting from α- sulfonyl acetamide via the formal [3+ 3] cycloaddition reaction of the latter into glutarimide. The pathway involves an efficient cycloaddition and regioselective reduction, and yields useful building blocks for heterocyclic chemistry.

 Related Synthetic Route
3-(3,4-dimethoxyphenyl)-1-propylpiperidin-2-one Structure

459453-71-5

3-(3,4-dimethox...

~89%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

3,4-Dimethoxyphenylmagnesium bromide Structure

89980-69-8

3,4-Dimethoxyph...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

Acetamide,2-chloro-N-propyl- Structure

13916-39-7

Acetamide,2-chl...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

N-propyl-2-(4-methylphenyl)sulfonylacetamide Structure

100370-83-0

N-propyl-2-(4-m...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

methyl 2-(3,4-dimethoxyphenyl)acrylate Structure

459453-60-2

methyl 2-(3,4-d...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

methyl 2-(3,4-dimethoxyphenyl)-2-hydroxypropanoate Structure

870262-21-8

methyl 2-(3,4-d...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

3-(3,4-dimethoxyphenyl)-5-[(4-methylphenyl)sulfonyl]-1-propyl-1,2,3,4-tetrahydropyridin-2-one Structure

459453-68-0

3-(3,4-dimethox...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

3-(3,4-dimethoxyphenyl)-5-[(4-methylphenyl)sulfonyl]-1-propylpiperidine-2,6-dione Structure

459453-64-6

3-(3,4-dimethox...

~%

3-(3,4-dimethoxyphenyl)-1-propylpiperidine Structure

62033-61-8

3-(3,4-dimethox...

Acetamide,2-chloro-N-propyl- Structure

13916-39-7

Acetamide,2-chl...

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

N-propyl-2-(4-methylphenyl)sulfonylacetamide Structure

100370-83-0

N-propyl-2-(4-m...

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

3-Methoxyphenylmagnesium bromide solution Structure

36282-40-3

3-Methoxyphenyl...

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

methyl 2-(3-methoxyphenyl)acrylate Structure

133033-14-4

methyl 2-(3-met...

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

(+/-)-methyl 2-hydroxy-2-(3-methoxyphenyl)propionate Structure

870262-18-3

(+/-)-methyl 2-...

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

N/A Structure

459453-66-8

N/A

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...

N/A Structure

459453-62-4

N/A

~%

3-(3-methoxyphenyl)-1-propylpiperidine Structure

86562-23-4

3-(3-methoxyphe...


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