3,4-Dihydro Naratriptan (Naratriptan Impurity B)

Base Information

• Chemical Name: 3,4-Dihydro Naratriptan (Naratriptan Impurity B)
• CAS No.: 121679-20-7
• Molecular Formula: C17H23N3O2S
• Molecular Weight: 333.455
• Mol file: 121679-20-7.mol

Synonyms:3,4-Dihydro Naratriptan (Naratriptan Impurity B);3,4-Dihydro Naratriptan;Naratriptan IMpurity B;N-Methyl-3-(1,2,3,6-tetrahydro-1-Methyl-4-pyridinyl)-1H-indole-5-ethanesulfonaMide

Chemical Property of 3,4-Dihydro Naratriptan (Naratriptan Impurity B)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 557.486°C at 760 mmHg
• Flash Point: 290.957°C
• PSA: 73.58000
• Density: 1.26g/cm³
• LogP: 3.38810
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

3,4-DihydroNaratriptan(NaratriptanImpurityB) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Naratriptan related compound B. Naratriptan impurity B.

Technology Process of 3,4-Dihydro Naratriptan (Naratriptan Impurity B)

There total 10 articles about 3,4-Dihydro Naratriptan (Naratriptan Impurity B) 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: 90.0%

1-Methyl-4-piperidone (1445-73-4) + N-Methyl-1H-indole-5-ethanesulphonamide (98623-50-8) → N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide (121679-20-7)

Guidance literature:

1-Methyl-4-piperidone; N-Methyl-1H-indole-5-ethanesulphonamide; With potassium hydroxide; In ethanol; Reflux;

With water; In ethanol; at 10 - 20 ℃; Product distribution / selectivity;

Reference yield:

2-(4-amino-phenyl)ethanesulfonic acid methylamide (98623-16-6) → N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide (121679-20-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C

2.1: dichloromethane / 1.5 h / 25 °C

3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C

3.2: 25 °C

4.1: potassium hydroxide; ethanol / 15 - 25 °C

5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C

5.2: 0.5 h / 25 °C

6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux

6.2: 10 - 15 °C / pH 8

With copper(l) iodide; ethanol; potassium tert-butylate; iodine; sodium hydrogencarbonate; trifluoroacetic acid; lithium chloride; potassium hydroxide; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.2: Sonogashira Coupling / 6.1: Aldol Condensation;

Reference yield:

N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide (1268265-90-2) → N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide (121679-20-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C

1.2: 25 °C

2.1: potassium hydroxide; ethanol / 15 - 25 °C

3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C

3.2: 0.5 h / 25 °C

4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux

4.2: 10 - 15 °C / pH 8

With copper(l) iodide; ethanol; potassium tert-butylate; trifluoroacetic acid; lithium chloride; potassium hydroxide; In 1-methyl-pyrrolidin-2-one; ethanol; N,N-dimethyl-formamide; 1.2: Sonogashira Coupling / 4.1: Aldol Condensation;

upstream raw materials:

1-Methyl-4-piperidone

N-Methyl-1H-indole-5-ethanesulphonamide

2-(4-amino-phenyl)ethanesulfonic acid methylamide

N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide

Downstream raw materials:

naratriptan

naratriptan hydrochloride

Refernces

• 1、 Behera, Ajaya Kumar,Majumdar, Poulomi,Mohanta, Prajna Parimita,Mishra, Sushanta Kumar. "An efficient synthetic protocol for the synthesis of 2-(1H-Indol-5-yl)-ethanesulfonic acid methylamide: A potential synthetic precursor for naratriptan and its novel 3-substituted derivatives". . p. 265 - 269. Retrieved 2018/04/20.
• 2、 -. "PROCESS FOR PREPARING INDOLE DERIVATIVES". Page/Page column 19. . Retrieved 2010/04/03.