Zimeldine

Base Information

• Chemical Name: Zimeldine
• CAS No.: 56775-88-3
• Molecular Formula: C16H17 Br N2
• Molecular Weight: 317.228
• UNII: 3J928617DW
• DSSTox Substance ID: DTXSID6048462
• Nikkaji Number: J14.273E
• Wikipedia: Zimelidine
• Wikidata: Q203483
• NCI Thesaurus Code: C152954
• Metabolomics Workbench ID: 149263
• ChEMBL ID: CHEMBL37744
• Mol file: 56775-88-3.mol

Synonyms:H 102 09;H-102-09;H10209;Hydrochloride, Zimeldine;Hydrochloride, Zimelidine;Zelmid;Zimeldine;Zimeldine Hydrochloride;Zimelidin;Zimelidine;Zimelidine Hydrochloride

Chemical Property of Zimeldine

Chemical Property:

• Vapor Pressure: 5.05E-07mmHg at 25°C
• Melting Point: 193°C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 412.8°Cat760mmHg
• Flash Point: 203.4°C
• PSA: 16.13000
• Density: 1.286g/cm³
• LogP: 5.44140
• Storage Temp.: Desiccate at RT
• Solubility.: 0.1 M HCl: 45 mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 316.05751
• Heavy Atom Count: 19
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

Zimeldine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC=C(C1=CC=C(C=C1)Br)C2=CN=CC=C2
• Isomeric SMILES: CN(C)C/C=C(/C1=CC=C(C=C1)Br)\C2=CN=CC=C2
• Uses: Zimeldine is a serotonin uptake inhibitor. Antidepressant. Zimelidine Dihydrochloride, is a selective 5-HT uptake inhibitor. It modulates nociception and induces hyperglycemia in vivo, and is an orally active antidepressant. Serotonin uptake inhibitor. Antidepressant
• Therapeutic Function: Antidepressant

Technology Process of Zimeldine

There total 30 articles about Zimeldine 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: 85.0%

N,N-dimethylammonium chloride (506-59-2) + (Z)-3-(4-bromophenyl)-3-(3-pyridyl)-2-propenal (77470-68-9) → Zimelidine (56775-88-3)

Guidance literature:

With sodium cyanoborohydride; In methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jo00196a021

Reference yield: 20.0%

N,N-dimethylammonium chloride (506-59-2) + (Z)-3-(4-bromophenyl)-3-(3-pyridyl)-2-propenal (77470-68-9) → (Z)-3-(4-bromophenyl)-3-(3-pyridinyl)prop-2-en-1-ol (77470-73-6) + 3-[(Z)-1-(4-Bromo-phenyl)-3-methoxy-propenyl]-pyridine (91671-10-2) + Zimelidine (56775-88-3)

Guidance literature:

With hydrogenchloride; molecular sieve; sodium cyanoborohydride; In methanol; for 20h; Ambient temperature;

DOI:10.1021/jo00196a021

Reference yield:

(4-bromophenyl)-pyridin-3-yl-methanone (14548-45-9) → Zimelidine (56775-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Zn / benzene / 1.) reflux, 2.) reflux, 4.5 h

2: 76 percent / LiAlH₄ / diethyl ether / 5 h / Heating

3: PBr₃ / CH₂Cl₂ / Heating

4: H₂O / 4 h / Ambient temperature

With lithium aluminium tetrahydride; phosphorus tribromide; zinc; In diethyl ether; dichloromethane; water; benzene;

DOI:10.3891/acta.chem.scand.36b-0091

upstream raw materials:

formaldehyd

Nomelidine

(4-bromophenyl)-pyridin-3-yl-methanone

[(dimethylamino)ethyl]triphenylphosphonium bromide

Downstream raw materials:

Nomelidine

(Z)-3-(4-bromophenyl)-3-(3-pyridyl)allylamine

(Z)-1-(4-bromophenyl)-3-pthalimido-1-(3-pyridyl)propene

I-ZIM

Refernces

• 1、 Hoegberg, Thomas,Ulff, Bengt. "Stereoconservative Reductive Methyl- and Dimethylamination of Isomeric 3,3-Diarylpropenals. Synthetic and Mechanistic Studies on Control of the Stereochemistry". . p. 4209 - 4214. Retrieved 2007/10/02.
• 2、 Baeckvall, Jan-E.,Nordberg, Ruth E.,Nystroem, Jan-E.,Hoegberg, Thomas,Ulff, Bengt. "Synthesis of 3-Aryl-3-pyridylallylamines Related to Zimelidine via Palladium-Catalyzed Amination". . p. 3479 - 3483. Retrieved 2007/10/02.