Lobelane

Base Information

• Chemical Name: Lobelane
• CAS No.: 530-51-8
• Molecular Formula: C₂₂H₂₉N
• Molecular Weight: 307.479
• DSSTox Substance ID: DTXSID601212781
• Nikkaji Number: J1.184.104J
• Wikidata: Q110624727
• Pharos Ligand ID: DJAM2HFDY75M
• ChEMBL ID: CHEMBL333465
• Mol file: 530-51-8.mol

Synonyms:lobelane

Chemical Property of Lobelane

Chemical Property:

• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 307.229999929
• Heavy Atom Count: 23
• Complexity: 284

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C(CCCC1CCC2=CC=CC=C2)CCC3=CC=CC=C3
• Isomeric SMILES: CN1[C@H](CCC[C@H]1CCC2=CC=CC=C2)CCC3=CC=CC=C3

Technology Process of Lobelane

There total 10 articles about Lobelane 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: 53.0%

(2S,6R)-1-Methyl-2,6-bis-((E)-styryl)-piperidine (758717-85-0) → N-methyl-2,6-di-(cis-phenylethyl)piperidine (530-51-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 18h; under 2327.17 Torr;

DOI:10.1021/jm0501228

Reference yield:

2-[(R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanol → N-methyl-2,6-di-(cis-phenylethyl)piperidine (530-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.22 g / H₃PO₄ / 60 °C

2: 53 percent / H₂ / Pd/C / methanol / 18 h / 2327.17 Torr

With phosphoric acid; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm0501228

Reference yield:

2-[(R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanone (946486-28-8) → N-methyl-2,6-di-(cis-phenylethyl)piperidine (530-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / ethanol / 20 °C

2: 3.22 g / H₃PO₄ / 60 °C

3: 53 percent / H₂ / Pd/C / methanol / 18 h / 2327.17 Torr

With sodium tetrahydroborate; phosphoric acid; hydrogen; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1021/jm0501228

upstream raw materials:

(2S,6R)-1-Methyl-2,6-bis-((E)-styryl)-piperidine

2-[(R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanone

(cis:trans)-(-)-lobeline

(S)-2-[(2S,6R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanol