N-Benzylcytisine

Base Information

• Chemical Name: N-Benzylcytisine
• CAS No.: 78867-61-5
• Molecular Formula: C₁₈H₂₀N₂O
• Molecular Weight: 280.37
• Nikkaji Number: J2.235.776J
• ChEMBL ID: CHEMBL508190
• Mol file: 78867-61-5.mol

Synonyms:N-Benzylcytisine;CHEMBL508190;Oprea1_691665;BDBM50279175;(1R,5S)-3-Benzyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

Chemical Property of N-Benzylcytisine

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 280.157563266
• Heavy Atom Count: 21
• Complexity: 476

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2CN(CC1C3=CC=CC(=O)N3C2)CC4=CC=CC=C4
• Isomeric SMILES: C1[C@H]2CN(C[C@@H]1C3=CC=CC(=O)N3C2)CC4=CC=CC=C4

Technology Process of N-Benzylcytisine

There total 23 articles about N-Benzylcytisine 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: 99.0%

benzyl bromide (100-39-0) + cytisine (485-35-8) → (1R,5S)-3-benzyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido-[1,2-a][1,5]diazocin-8-one (78867-61-5,109667-42-7)

Guidance literature:

With potassium carbonate; In acetonitrile; for 20h; Reflux;

DOI:10.1039/c8ob01456f

Reference yield: 84.0%

Methanesulfonic acid (3'R,5'S)-1'-benzyl-6-methoxy-1',2',3',4',5',6'-hexahydro-[2,3']bipyridinyl-5'-ylmethyl ester → 3-benzyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (78867-61-5,109667-42-7)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1021/ol0067538

Reference yield: 77.6%

cytisine (485-35-8) → (1R,5S)-3-benzyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido-[1,2-a][1,5]diazocin-8-one (78867-61-5,109667-42-7)

Guidance literature:

In acetone; Heating;

DOI:10.1016/S0014-827X(99)00049-X

upstream raw materials:

benzyl chloride

cytisine

benzyl bromide

benzaldehyde

Refernces

• 1、 Chuyko, Alexey,Dolgonos, Grygoriy,Fetyukhin, Volodymyr,Lukin, Oleg,Shivanyuk, Alexander. "Simple Synthesis of Complex Amines from the Diels-Alder Adducts of (-)-Cytisine". . . Retrieved 2021/08/25.
• 2、 Dixon, Amanda J.,McGrath, Matthew J.,O’Brien, Peter,Holle, Sigrid,Fürstner, Alois. "Synthesis of (+)-(1R,2S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]Tridecane, A (+)-sparteine surrogate". . p. 141 - 154. Retrieved 2017/09/30.