3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Base Information

• Chemical Name: 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate
• CAS No.: 1403385-11-4
• Molecular Formula: C₃₀H₃₄ClN₃O₃
• Molecular Weight: 520.071

Synonyms:3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Chemical Property of 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Chemical Property:

Purity/Quality:

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Technology Process of 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

There total 7 articles about 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate 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: 17.0%

3-Dimethylamino-1-propanol (3179-63-3) + 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (1300031-52-0) → 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (1403385-11-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1300031-98-4) → 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (1403385-11-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 6 h / 105 °C / Inert atmosphere

2.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 - 6 °C

2.2: 0.51 h / 0 °C

3.1: sodium t-butanolate / DavePhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 16 h / 70 °C / Inert atmosphere

4.1: sodium hydroxide; water / ethanol / 2 h / 20 °C

5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

With dmap; aluminum (III) chloride; water; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; DavePhos; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

1-methylethyl {(3S)-3-[(4-bromophenyl)amino]butanoyl}carbamate (1300031-94-0) → 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (1403385-11-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate / ethanol; water / 2 h / -10 - 20 °C

2.1: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 6 h / 105 °C / Inert atmosphere

4.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 - 6 °C

4.2: 0.51 h / 0 °C

5.1: sodium t-butanolate / DavePhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 16 h / 70 °C / Inert atmosphere

6.1: sodium hydroxide; water / ethanol / 2 h / 20 °C

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

With pyridine; dmap; aluminum (III) chloride; sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; DavePhos; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

3-Dimethylamino-1-propanol

4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid

1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

1-methylethyl [(2S,4R)-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

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