Ecopipam

Base Information

• Chemical Name: Ecopipam
• CAS No.: 112108-01-7
• Molecular Formula: C19H20 Cl N O
• Molecular Weight: 313.827
• UNII: 0X748O646K
• DSSTox Substance ID: DTXSID8043814
• Nikkaji Number: J323.080E
• Wikipedia: Ecopipam
• Wikidata: Q5333851
• NCI Thesaurus Code: C74188
• Pharos Ligand ID: FLU79HFK3G6B
• Metabolomics Workbench ID: 153292
• ChEMBL ID: CHEMBL298406
• Mol file: 112108-01-7.mol

Synonyms:6,7,7a,8,9,13b-hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo(d)naphtho-(2,1b)azepine;ecopipam;Sch 39166;Sch-39166;Sch39166

Chemical Property of Ecopipam

Chemical Property:

• Vapor Pressure: 8.75E-09mmHg at 25°C
• Boiling Point: 451.9°Cat760mmHg
• PKA: 8.73±0.20(Predicted)
• Flash Point: 227.1°C
• PSA: 23.47000
• Density: 1.22g/cm³
• LogP: 3.91810
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 313.1233420
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C3C1CCC4=CC=CC=C34)O)Cl
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@@H]3[C@@H]1CCC4=CC=CC=C34)O)Cl
• Recent ClinicalTrials: Ecopipam Tablets to Study Tourette Syndrome in Children and Adolescents - Open Label Extension
• Recent EU Clinical Trials: A Multicenter, Placebo-Controlled, Double-Blind, Randomized, Parallel-Group, Phase 2b Study to Evaluate the Efficacy and Safety of Ecopipam Tablets in Children and Adolescent Subjects with Tourette’s Syndrome

Technology Process of Ecopipam

There total 34 articles about Ecopipam 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: 89.0%

trans-(-)-(6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-12-methoxy-5H-benzonaphth<2,1-b>azepine → ecopipam (112108-01-7,112107-92-3)

Guidance literature:

With hydrogen bromide; acetic acid; at 130 ℃; for 7h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

1,2-Dihydronaphthalene (447-53-0) → ecopipam (112108-01-7,112107-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hydrogencarbonate / methanol; acetonitrile / 0.08 h / Inert atmosphere

1.2: 17 h / 25 - 30 °C / Inert atmosphere

2.1: Teflon acid / 20 h / Autoclave; Heating; Inert atmosphere

3.1: n-butyllithium; p-toluenesulfonyl chloride; 1,10-Phenanthroline / tetrahydrofuran / Inert atmosphere

3.2: Inert atmosphere

4.1: methanesulfonic acid / dichloromethane / 69 h / 0 - 40 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: Di-p-toluoyl-L-tartaric acid / Resolution of racemate; Inert atmosphere

5.2: Inert atmosphere

With n-butyllithium; 1,10-Phenanthroline; methanesulfonic acid; Di-p-toluoyl-L-tartaric acid; potassium hydrogencarbonate; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/op970121s

Reference yield:

1,2-epoxy-3,4-dihydronaphthalene (2461-34-9) → ecopipam (112108-01-7,112107-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Teflon acid / 20 h / Autoclave; Heating; Inert atmosphere

2.1: n-butyllithium; p-toluenesulfonyl chloride; 1,10-Phenanthroline / tetrahydrofuran / Inert atmosphere

2.2: Inert atmosphere

3.1: methanesulfonic acid / dichloromethane / 69 h / 0 - 40 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

4.1: Di-p-toluoyl-L-tartaric acid / Resolution of racemate; Inert atmosphere

4.2: Inert atmosphere

With n-butyllithium; 1,10-Phenanthroline; methanesulfonic acid; Di-p-toluoyl-L-tartaric acid; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/op970121s

upstream raw materials:

3-phenyl-propionaldehyde

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene

(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

C₂₄H₂₃ClN₂O₅S

Downstream raw materials:

6,6aS,7,8,9,13bR-hexahydro-7-methyl-11-nitro-N-phenylmethyl-5H-benzo[d]naphth[2,1-b]azepin-12-amine

Refernces

• 1、 Draper, Richard W.,Hou, Donald. "Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 1. aziridinium salt based syntheses". . p. 175 - 185. Retrieved 2013/09/08.