3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

Base Information

Chemical Name:3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile
CAS No.:264264-27-9
Molecular Formula:C₁₉H₂₇N₃
Molecular Weight:297.443
Hs Code.:

3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>d</i>]azepine-7-carbonitrile

Synonyms:3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

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Chemical Property of 3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

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Technology Process of 3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

There total 8 articles about 3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile 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: 100.0%

: 264264-24-6
{4-[2-(7-cyano-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

: 264264-27-9
3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1016/S0960-894X(00)00505-9

Reference yield:

: 36133-00-3
2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

: 264264-27-9
3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / Et₃N / tetrahydrofuran; H₂O / 18 h / 20 °C

2: 92 percent / Et₃N / CH₂Cl₂ / 18 h / -20 °C

3: 97 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 100 °C

4: 100 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

5: 80 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 18 h / 0 °C

6: 100 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Acylation / 2: sulfonylation / 3: Substitution / 4: acidolysis / 5: reductive alkylation / 6: acidolysis;
DOI:10.1016/S0960-894X(00)00505-9

Reference yield:

: 50351-80-9
7-methoxy-2,3,4,5-tetrahydro-1H-benz[d]azepine

: 264264-27-9
3-[2-(4-amino-cyclohexyl)-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7-carbonitrile

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / 48 percent aq. HBr / 3 h / Heating

2: 93 percent / Et₃N / tetrahydrofuran; H₂O / 18 h / 20 °C

3: 92 percent / Et₃N / CH₂Cl₂ / 18 h / -20 °C

4: 97 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 100 °C

5: 100 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

6: 80 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 18 h / 0 °C

7: 100 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; sodium tris(acetoxy)borohydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: demethylation / 2: Acylation / 3: sulfonylation / 4: Substitution / 5: acidolysis / 6: reductive alkylation / 7: acidolysis;
DOI:10.1016/S0960-894X(00)00505-9