1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole

Base Information

• Chemical Name: 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole
• CAS No.: 1017279-20-7
• Molecular Formula: C₂₅H₂₅ClN₂O₂
• Molecular Weight: 420.939

Synonyms:1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole

Chemical Property of 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole

Chemical Property:

Purity/Quality:

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Technology Process of 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole

There total 2 articles about 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole 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: 62.0%

(E)-4-(dimethylaminomethyl)cinnamic acid hydrochloride (1017278-95-3) + 3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzindole (122745-41-9) → 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (1017279-20-7)

Guidance literature:

3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzindole; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h;

(E)-4-(dimethylaminomethyl)cinnamic acid hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2011.12.007

Reference yield:

methyl (E)-4-(dimethylaminomethyl)cinnamate (1017279-66-1) → 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (1017279-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / methanol; water / 2 h / Reflux

1.2: 20 °C

2.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

2.2: 16 h / 20 °C

With hydrogenchloride; sodium hydroxide; In 1,4-dioxane; methanol; water;

DOI:10.1016/j.bmc.2011.12.007

Reference yield: 78.0%

2-(bromomethyl)-1-methyl-5-nitro-1H-pyrrole (1017279-01-4) + 1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (1017279-20-7) → (E)-N-(4-(3-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide (1357580-60-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 432h; Darkness;

DOI:10.1016/j.bmc.2011.12.007

upstream raw materials:

(E)-4-(dimethylaminomethyl)cinnamic acid hydrochloride

3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzindole

methyl (E)-4-(dimethylaminomethyl)cinnamate

Downstream raw materials:

(E)-N-(4-(3-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide

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