Pravadoline

Base Information

• Chemical Name: Pravadoline
• CAS No.: 92623-83-1
• Molecular Formula: C23H26N2O3
• Molecular Weight: 378.471
• Hs Code.: 2934999090
• UNII: P3JW662TWA
• DSSTox Substance ID: DTXSID2046127
• Nikkaji Number: J360.174I
• Wikipedia: Pravadoline
• Wikidata: Q7238828
• NCI Thesaurus Code: C84104
• ChEMBL ID: CHEMBL13178
• Mol file: 92623-83-1.mol

Synonyms:pravadoline;pravadoline maleate;WIN 48098-6

Chemical Property of Pravadoline

Chemical Property:

• Vapor Pressure: 2.81E-12mmHg at 25°C
• Melting Point: 104-105 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Refractive Index: 1.603
• Boiling Point: 553.1 °C at 760 mmHg
• PKA: 7.07±0.10(Predicted)
• Flash Point: 288.3 °C
• PSA: 43.70000
• Density: 1.18 g/cm³
• LogP: 3.45940
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 378.19434270
• Heavy Atom Count: 28
• Complexity: 514

Purity/Quality:

99.0% ^*data from raw suppliers

(4-Methoxyphenyl)(2-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)methanone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1CCN3CCOCC3)C(=O)C4=CC=C(C=C4)OC
• Uses: An antiinflammatory and analgesic drug. Cannabinoid receptor agonist

Technology Process of Pravadoline

There total 27 articles about Pravadoline 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: 96.0%

N-(2-bromoethyl)morpholine (89583-07-3) + 2-methyl-3-(4-methoxybenzoyl)indole (26211-90-5) → pravadoline (92623-83-1)

Guidance literature:

2-methyl-3-(4-methoxybenzoyl)indole; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

N-(2-bromoethyl)morpholine; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03383

Reference yield: 90.0%

2-(morpholin-4-yl)ethanol (622-40-2) + 1-methylsulfonyl-2-methyl-3-(4-methoxybenzoyl)-1H-indole (137641-88-4) → pravadoline (92623-83-1)

Guidance literature:

With sodium hydride; potassium carbonate; In toluene; at 100 ℃; for 2h;

DOI:10.1016/0040-4039(95)00229-6

Reference yield: 85.0%

tert-butyl (2-methyl-1-(2-morpholinoethyl)-1H-indole-3-carbonyl)(phenyl)carbamate + 4-methoxyphenyl magnesium bromide (13139-86-1) → pravadoline (92623-83-1)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03447

upstream raw materials:

2-methyl-3-(4-methoxybenzoyl)indole

4-(2-chloroethyl)morpholine hydrochride

2-(morpholin-4-yl)ethanol

1-methylsulfonyl-2-methyl-3-(4-methoxybenzoyl)-1H-indole

Refernces

• 1、 Xia, Ji-Bao,Yang, Yusheng,Yu, Zhi-Xiang,Zhang, Zheng-Bing. "Lewis Base-Catalyzed Amino-Acylation of Arylallenes via C-N Bond Cleavage: Reaction Development and Mechanistic Studies". . p. 5419 - 5429. Retrieved 2020/09/02.
• 2、 -. "Metal-free 3-acyl indole compound synthetic method". Paragraph 0061. . Retrieved 2019/12/09.