Spiramide

Base Information

• Chemical Name: Spiramide
• CAS No.: 510-74-7
• Molecular Formula: C22H26 F N3 O2
• Molecular Weight: 383.466
• Hs Code.: 2933990090
• UNII: 471LF4O004
• DSSTox Substance ID: DTXSID6042579
• Nikkaji Number: J8.666E
• Wikipedia: Spiramide
• Wikidata: Q7577785
• NCI Thesaurus Code: C66559
• Pharos Ligand ID: P3T9XL4L7DJ8
• Metabolomics Workbench ID: 63234
• ChEMBL ID: CHEMBL79834
• Mol file: 510-74-7.mol

Synonyms:8-(3-(4-Fluorophenoxy) propyl)-1-phenyl-1,3,8-triazaspiro(4, 5)decan-4-one;AMI-193;spiramide;spiramide hydrochloride;spiramide monohydrochloride

Chemical Property of Spiramide

Chemical Property:

• Vapor Pressure: 8.83E-15mmHg at 25°C
• Boiling Point: 609.1 ºC at 760 mmHg
• Flash Point: 322.2 ºC
• PSA: 44.81000
• Density: 1.26 g/cm³
• LogP: 3.35480
• Storage Temp.: Store at RT
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 383.20090524
• Heavy Atom Count: 28
• Complexity: 510

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

AMI-193 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN(CCC12C(=O)NCN2C3=CC=CC=C3)CCCOC4=CC=C(C=C4)F
• Uses: AMI-193 is a selective 5-HT2A and D2DR receptor antagonist. Endoplasmic reticulum (ER) stress inducer; Also, it is derived from 4-Fluorophenol (F595325), which is a fluorinated phenolic compound with various applications as an starting reagent for the synthesis of pharmaceutical goods.

Technology Process of Spiramide

There total 2 articles about Spiramide 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: 87.0%

1-(3-chloropropoxy)-4-fluorobenzene (1716-42-3) + 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1021-25-6) → Spiramide (510-74-7)

Guidance literature:

With diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 17h; Inert atmosphere;

DOI:10.1021/jo400646k

Reference yield:

→ Spiramide (510-74-7)

Guidance literature:

aus d. Decan (III,R¹=Ph,R²=R³=H) und 1-Chlor-3-(4-fluorphenoxy)propan;

Reference yield: 89.0%

1-Bromo-11-hydroxyundecane (1611-56-9) + Spiramide (510-74-7) → 3-[11-hydroxyundecyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one (1446684-97-4)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 120 ℃; Inert atmosphere;

DOI:10.1021/jo400646k

upstream raw materials:

1-(3-chloropropoxy)-4-fluorobenzene

1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Downstream raw materials:

3-[2-(2-(2-hydroxyethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

3-[2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)-propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

3-[2-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)-propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

3-[11-(tosyloxy)undecyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

Refernces

• 1、 Ismaiel,De los Angeles,Teitler,Ingher,Glennon. "Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT(1C)-selective antagonist". . p. 2519 - 2525. Retrieved 2007/10/02.