(1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide

Base Information

• Chemical Name: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide
• CAS No.: 177793-79-2
• Molecular Formula: C18H24N2O
• Molecular Weight: 284.39600
• Mol file: 177793-79-2.mol

Synonyms:(1S)-N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-1,2,3,4-tetrahydro-1-na phthalenecarboxamide

Chemical Property of (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide

Chemical Property:

• Boiling Point: 495.3±34.0 °C(Predicted)
• PKA: 14.98±0.20(Predicted)
• PSA: 35.83000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 3.09510
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide

There total 9 articles about (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxamide 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%

(S)-(-)-1,2,3,4-tetrahydro-1-naphthoyl chloride + (S)-3-aminoquinuclidine (120570-05-0,781591-76-2) → N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide (177793-79-2,177793-81-6)

Guidance literature:

In toluene; at 70 ℃; for 1.5h; Industrial scale;

Reference yield: 76.4%

(S)-3-aminoquinuclidine hydrochloride + (S)-(-)-1,2,3,4-tetrahydro-1-naphthoyl chloride → N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide (177793-79-2,177793-81-6)

Guidance literature:

In ethyl acetate; at 20 ℃; for 2h;

Reference yield: 75.0%

tetralin-1-carboxylic acid (1914-65-4) + (S)-3-aminoquinuclidine (120570-05-0,781591-76-2) → N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide (177793-79-2,177793-81-6)

Guidance literature:

tetralin-1-carboxylic acid; With thionyl chloride; N,N-dimethyl-formamide; In toluene; at 20 - 50 ℃; for 2h;

(S)-3-aminoquinuclidine; In ethyl acetate; toluene; at 50 ℃; for 1h; Temperature;

upstream raw materials:

tetralin-1-carboxylic acid

(S)-3-aminoquinuclidine

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride

Downstream raw materials:

palonosetron hydrochloride

palonosetron

C₁₈H₂₆N₂

(1-azabicyclo[2.2.2]oct-3-yl)-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)amine

Refernces

• 1、 -. "Hydrochloric acid palonosetron and intermediate preparation method (by machine translation)". . . Retrieved 2018/07/07.
• 2、 -. "A hydrochloric acid palonosetron production method". Paragraph 0048-0050. . Retrieved 2017/08/25.