Spiperone

Base Information

• Chemical Name: Spiperone
• CAS No.: 749-02-0
• Molecular Formula: C23H26 F N3 O2
• Molecular Weight: 395.477
• European Community (EC) Number: 212-024-0
• NSC Number: 757864,170983
• UNII: 4X6E73CJ0Q
• DSSTox Substance ID: DTXSID5045205
• Nikkaji Number: J3.320K
• Wikipedia: Spiperone
• Wikidata: Q3077150
• NCI Thesaurus Code: C66558
• Pharos Ligand ID: PQK3PXF7RT12
• Metabolomics Workbench ID: 53447
• ChEMBL ID: CHEMBL267930
• Mol file: 749-02-0.mol

Synonyms:Spiperone;Spiroperidol;Spiroperone

Chemical Property of Spiperone

Chemical Property:

• Vapor Pressure: 8.2E-16mmHg at 25°C
• Melting Point: 190-193.60C
• Boiling Point: 630.6°C at 760 mmHg
• PKA: pKa 8.31 (Uncertain);9.09 (Uncertain)
• Flash Point: 335.2°C
• PSA: 52.65000
• Density: 1.1714 (estimate)
• LogP: 3.54880
• Storage Temp.: Store at RT
• Solubility.: H2O: slightly soluble0.2mg/mL
• Water Solubility.: 32mg/L(22 oC)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 395.20090524
• Heavy Atom Count: 29
• Complexity: 577

Purity/Quality:

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

Spiperone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-63
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCC12C(=O)NCN2C3=CC=CC=C3)CCCC(=O)C4=CC=C(C=C4)F
• Uses: Spiperone is an antipsychotic. Antipsychotic antibacterial
• Therapeutic Function: Tranquilizer

Technology Process of Spiperone

There total 8 articles about Spiperone 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: 93.0%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2,41167-07-1) + 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1021-25-6) → spiperone (749-02-0)

Guidance literature:

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

DOI:10.1021/jo400646k

Reference yield: 45.0%

8-<4-(4-nitrophenyl)-4-oxobutyl>-1-phenyl-1,3,8-triazaspiro<4.5>decan-4-one (85562-17-0) → spiperone (749-02-0)

Guidance literature:

With hydrogen fluoride; potassium oxalate; potassium carbonate; [2.2.2]cryptande; In dimethyl sulfoxide; Heating;

DOI:10.1246/bcsj.70.681

Reference yield:

(4-aminophenyl)(cyclopropyl)methanone (57189-90-9) → spiperone (749-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) HBF₄, NaNO₂, 2) Cu, NaNO₂ / 1) H₂O, 30 min, 2) H₂O, 1 h

2: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C

3: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C

4: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating

With hydrogenchloride; tetrafluoroboric acid; hydrogen fluoride; potassium oxalate; copper; potassium carbonate; [2.2.2]cryptande; potassium iodide; sodium nitrite; In methanol; dimethyl sulfoxide; toluene;

DOI:10.1246/bcsj.70.681

upstream raw materials:

8-<4-(4-nitrophenyl)-4-oxobutyl>-1-phenyl-1,3,8-triazaspiro<4.5>decan-4-one

(4-aminophenyl)(cyclopropyl)methanone

1-(4-acetylaminophenyl)-4-chloro-1-butanone

Acetanilid

Downstream raw materials:

3-Allyl-8-[4-(4-fluoro-phenyl)-4-oxo-butyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-3-[4-(N-tert-butoxycarbonyl)aminophenethyl]-1,3,8-triazaspiro[4.5]decan-4-one

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

8-[4-(4-fluorophenyl)-4-oxobutyl]-3-[¹¹C]methyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one