N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide

Base Information

• Chemical Name: N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide
• CAS No.: 1356458-16-6
• Molecular Formula: C₂₅H₂₇N₃O₂
• Molecular Weight: 407.461

Synonyms:N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide

Chemical Property of N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide

Chemical Property:

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Technology Process of N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide

There total 4 articles about N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([⁽²⁾H₆]quinolin-8-yl)methyl)benzamide 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: 78.0%

t-butyl 4-((4-((2-hydroxyethyl)(methyl)carbamoyl)phenyl)([(2)H6]quinolin-8-yl)methylene)piperidine-1-carboxylate (1356458-15-5) → N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([(2)H6]quinolin-8-yl)methyl)benzamide (1356458-16-6)

Guidance literature:

t-butyl 4-((4-((2-hydroxyethyl)(methyl)carbamoyl)phenyl)([⁽²⁾H₆]quinolin-8-yl)methylene)piperidine-1-carboxylate; With hydrogenchloride; In 1,4-dioxane; methanol; dichloromethane; for 0.333333h;

With sodium carbonate; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1002/jlcr.1939

Reference yield:

[(2)H6]quinolin-8-ol (112465-97-1) → N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([(2)H6]quinolin-8-yl)methyl)benzamide (1356458-16-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / dichloromethane / 1.17 h / 0 - 20 °C

2.1: 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; bis(pinacol)diborane / 1,4-dioxane / 80 °C / Inert atmosphere

2.3: pH 7

3.1: palladium diacetate; potassium carbonate / water; acetonitrile / 76 °C

4.1: hydrogenchloride / 1,4-dioxane; methanol; dichloromethane / 0.33 h

With pyridine; hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; palladium diacetate; potassium carbonate; bis(pinacol)diborane; In 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 3.1: Suzuki coupling;

DOI:10.1002/jlcr.1939

Reference yield:

[(2)H6]quinolin-8-yl trifluoromethanesulfonate (1356458-13-3) → N-(2-hydroxyethyl)-N-methyl-4-(piperidin-4-ylidene([(2)H6]quinolin-8-yl)methyl)benzamide (1356458-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; bis(pinacol)diborane / 1,4-dioxane / 80 °C / Inert atmosphere

1.3: pH 7

2.1: palladium diacetate; potassium carbonate / water; acetonitrile / 76 °C

3.1: hydrogenchloride / 1,4-dioxane; methanol; dichloromethane / 0.33 h

With hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; palladium diacetate; potassium carbonate; bis(pinacol)diborane; In 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 2.1: Suzuki coupling;

DOI:10.1002/jlcr.1939

upstream raw materials:

[⁽²⁾H₆]quinolin-8-ol

[⁽²⁾H₆]quinolin-8-yl trifluoromethanesulfonate

[⁽²⁾H₆]quinolin-8-ylboronic acid

t-butyl 4-((4-((2-hydroxyethyl)(methyl)carbamoyl)phenyl)([⁽²⁾H₆]quinolin-8-yl)methylene)piperidine-1-carboxylate

Downstream raw materials:

N-(2-hydroxyethyl)-N-methyl-4-([⁽²⁾H₆]quinolin-8-yl(1-(thiazol-4-ylmethyl)piperidin-4-ylidene)methyl)benzamide

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