4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester
CAS No.:178309-56-3
Molecular Formula:C₃₂H₄₂Cl₂N₄O₃
Molecular Weight:601.616
Hs Code.:

4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

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Chemical Property of 4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

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Technology Process of 4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

There total 7 articles about 4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 18.0%

: 178311-27-8
1-benzyl-5-(3,4-dichlorophenyl)-5-formylmethyl-2-piperidone

: 178312-58-8
tert-butyl 4-(3-azetidinyl)-1-piperazinecarboxylate hydrochloride

: 178309-56-3
4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: 1-benzyl-5-(3,4-dichlorophenyl)-5-formylmethyl-2-piperidone; tert-butyl 4-(3-azetidinyl)-1-piperazinecarboxylate hydrochloride; With triethylamine; In tetrahydrofuran; for 1h;

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 20 ℃; for 16h; Further stages.;
DOI:10.1021/jm0209331

Reference yield:

: 3218-49-3
3,4-dichloro-benzeneacetonitrile

: 178309-56-3
4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.5 h

1.2: 34 percent / tetrahydrofuran / 20 °C

2.1: LDA / tetrahydrofuran / -78 - 20 °C

2.2: 61 percent / tertbutylammonium iodide / tetrahydrofuran / 20 °C

3.1: 75 percent / H₂; NH₃ / Raney nickel / ethanol / 14 h / 20 °C

4.1: NaH / dimethylformamide / 0.67 h / 20 °C

4.2: 91 percent / dimethylformamide / 0.5 h / 0 °C

5.1: HCl; methanol / 2 h / 20 °C

6.1: 9.47 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: Et₃N / tetrahydrofuran / 1 h

7.2: 18 percent / sodium triacetoxyborohydride; AcOH / tetrahydrofuran / 16 h / 20 °C

With hydrogenchloride; methanol; oxalyl dichloride; ammonia; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; nickel; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern reaction;
DOI:10.1021/jm0209331

Reference yield:

: 135936-16-2
α-[2-(Tetrahydropyran-2-yloxy)ethyl]-3,4-dichlorophenyl-acetonitrile

: 178309-56-3
4-(1-{2-[1-benzyl-3-(3,4-dichloro-phenyl)-6-oxo-piperidin-3-yl]-ethyl}-azetidin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / -78 - 20 °C

1.2: 61 percent / tertbutylammonium iodide / tetrahydrofuran / 20 °C

2.1: 75 percent / H₂; NH₃ / Raney nickel / ethanol / 14 h / 20 °C

3.1: NaH / dimethylformamide / 0.67 h / 20 °C

3.2: 91 percent / dimethylformamide / 0.5 h / 0 °C

4.1: HCl; methanol / 2 h / 20 °C

5.1: 9.47 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: Et₃N / tetrahydrofuran / 1 h

6.2: 18 percent / sodium triacetoxyborohydride; AcOH / tetrahydrofuran / 16 h / 20 °C

With hydrogenchloride; methanol; oxalyl dichloride; ammonia; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; nickel; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern reaction;
DOI:10.1021/jm0209331