2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

Base Information

Chemical Name:2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile
CAS No.:1200184-86-6
Molecular Formula:C₂₃H₂₅N₃O₃
Molecular Weight:391.47
Hs Code.:

Synonyms:2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

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Chemical Property of 2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

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Technology Process of 2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

There total 3 articles about 2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile 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:

: 111373-03-6
2-(piperazin-1-yl)benzonitrile

: 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene

: 1200184-86-6
2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

: 2-{4-[(1R,2R)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

Guidance literature:: With ammonium iodide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; In tetrahydrofuran; at 80 ℃; for 24h; Overall yield = 77 %; Overall yield = 74 mg; enantioselective reaction;
DOI:10.3390/molecules201219748

Reference yield:

: 37895-73-1
1,2-dibromo-4,5-dimethoxybenzene

: 1200184-86-6
2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C / Inert atmosphere

2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; ammonium iodide / tetrahydrofuran / 24 h / 80 °C

With ammonium iodide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; n-butyllithium; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; In tetrahydrofuran; hexane; 1: |Diels-Alder Cycloaddition;
DOI:10.3390/molecules201219748

Reference yield:

: 19061-37-1
1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene

: 111373-03-6
2-(piperazin-1-yl)benzonitrile

: 1200184-86-6
2-{4-[(1S,2S)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

: 2-{4-[(1R,2R)-1-hydroxy-6,7-dimethoxy-1,2-dihydronaphthalen-2-yl]-piperazin-1-yl}-benzonitrile

Guidance literature:: With ammonium iodide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; In tetrahydrofuran; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Reflux;
DOI:10.3762/bjoc.5.53