N-Methylconanin-5-en-3β-amine

Base Information

• Chemical Name: N-Methylconanin-5-en-3β-amine
• CAS No.: 468-36-0
• Molecular Formula: C₂₃H₃₈N₂
• Molecular Weight: 342.568
• Mol file: 468-36-0.mol

Synonyms:

Chemical Property of N-Methylconanin-5-en-3β-amine

Chemical Property:

• Melting Point: 92°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: A pregnene type alkaloid found in the bark and seeds of Holarrhena antidysenterica Wall., the base yields a hydrate, m.p. 88-92°C and has [α]25D + 30.0° (aqueous EtOH). It is freely soluble in most organic solvents. It yields a series of crystalline salts and derivatives, e.g. the hydrochloride, m.p. 334-335°C (dec.); hydrobromide, m.p. 344°C; hydriodide, m.p. 316°C; platinichloride, m.p. 285°C (dec.); methiodide, m.p. 290°C (dec.) and the picrate, m.p. 198-200°C. The N-acetyl derivative has also been prepared, m.p. 161°C yielding a hydrochloride, m.p. 325-6°C, as has the benzoyl compound, m.p. l59-l60°C, also forming a hydrochloride, m.p. 325-6°C (dec.). On methylation, the alkaloid yields conessine and heating with dilute H2S04 isomerizes the base to isonorisoconessine, [0:]5S + 101 ° (EtOH), furnishing a hydriodide, m.p. 289°C (dec.) and a picrate, m.p. 166°C.

Technology Process of N-Methylconanin-5-en-3β-amine

There total 6 articles about N-Methylconanin-5-en-3β-amine 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: 75.0%

methyl-((3S,3aS,5aS,5bR,9S,11aR,11bS,13aR)-2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentalenol[1,6a-a]phenanthren-9-yl)-carbamic acid 2,2,2-trichloro-ethyl ester → methyl-((3S,3aS,5aS,5bR,9S,11aR,13aR)-2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentalenol[1,6a-a]phenanthren-9-yl)-amine (468-36-0,33276-40-3)

Guidance literature:

With cadmium-lead couple; ammonium acetate; In tetrahydrofuran;

Reference yield: 75.0%

conessine (510-73-6,546-06-5,7013-59-4,14152-37-5,14546-12-4,47469-35-2) → methyl-((3S,3aS,5aS,5bR,9S,11aR,13aR)-2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentalenol[1,6a-a]phenanthren-9-yl)-amine (468-36-0,33276-40-3)

Guidance literature:

With palladium 10% on activated carbon; ammonium acetate; In tetrahydrofuran; water;

DOI:10.1021/jm8003625

Reference yield: 55.0%

C24H40N2O → methyl-((3S,3aS,5aS,5bR,9S,11aR,13aR)-2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentalenol[1,6a-a]phenanthren-9-yl)-amine (468-36-0,33276-40-3)

Guidance literature:

With ferrous(II) sulfate heptahydrate; In methanol; at 20 ℃; for 12h;

DOI:10.1002/cjoc.201300441

upstream raw materials:

conessine

Refernces

• 1、 Zhao, Chen,Sun, Minghua,Bennani, Youssef L.,Gopalakrishnan, Sujatha M.,Witte, David G.,Miller, Thomas R.,Krueger, Kathleen M.,Browman, Kaitlin E.,Thiffault, Christine,Wetter, Jill,Marsh, Kennan C.,Hancock, Arthur A.,Esbenshade, Timothy A.,Cowart, Marlon D.. "The alkaloid conessine and analogues as potent histamine H3 receptor antagonists". experimental part. p. 5423 - 5430. Retrieved 2009/07/01.
• 2、 -. "AZACYCLOSTEROID HISTAMINE-3 RECEPTOR LIGANDS". Page/Page column 52; 53. . Retrieved 2010/02/14.