Pyrrobutamine

Base Information

• Chemical Name: Pyrrobutamine
• CAS No.: 91-82-7
• Molecular Formula: C₂₀H₂₂ClN
• Molecular Weight: 311.854
• European Community (EC) Number: 202-101-7
• Nikkaji Number: J4.644B,J257.438A
• Wikipedia: Pyrrobutamine
• Wikidata: Q63395560
• NCI Thesaurus Code: C81146
• Mol file: 91-82-7.mol

Synonyms:1-(gamma-p-chlorobenzylcinnamyl)pyrrolidine;pirrobutamine;pyrrobutamine;pyrrobutamine, (Z)-isomer;pyrrobutamine, hydrobromide salt, (Z)-isomer;pyrrobutamine, phosphate (1:2) salt;pyrrobutamine, phosphate (1:2) salt, (E)-isomer;pyrrobutamine, phosphate (2:1) salt, (trans)-isomer

Chemical Property of Pyrrobutamine

Chemical Property:

• Vapor Pressure: 5.3E-08mmHg at 25°C
• Melting Point: 48-49°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 441.8°C at 760 mmHg
• PKA: pKa 8.77(H2O t=25 c=0.002 to 0.01) (Uncertain)
• Flash Point: 221°C
• PSA: 3.24000
• Density: 1.118g/cm³
• LogP: 4.99980
• Solubility.: Dichloromethane
• Water Solubility.: 271.3mg/L(37.5 oC)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 311.1440774
• Heavy Atom Count: 22
• Complexity: 345

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pyrrobutamine(MixtureofE/Z) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)CC=C(CC2=CC=C(C=C2)Cl)C3=CC=CC=C3
• Isomeric SMILES: C1CCN(C1)C/C=C(/CC2=CC=C(C=C2)Cl)\C3=CC=CC=C3
• Uses: Antihistaminic. Pyrrobutamine is an intermediate in the synthesis of Pyrrobutamine Hydrochloride (P997800), which is an antihistaminic.

Technology Process of Pyrrobutamine

There total 4 articles about Pyrrobutamine 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:

1-(4-chloro-phenyl)-2-phenyl-4-pyrrolidino-butan-2-ol (77-64-5) → Pyrrobutamin (51658-04-9,91-82-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1111/j.2042-7158.1970.tb08518.x

Reference yield:

1-phenyl-3-(pyrrolidin-1-yl)propan-1-one (94-39-3) → Pyrrobutamin (51658-04-9,91-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: concentrated aqueous hydrochloric acid

With hydrogenchloride; diethyl ether;

Reference yield:

acetophenone (98-86-2) → Pyrrobutamin (51658-04-9,91-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrochloric acid; ethanol

2: diethyl ether

3: concentrated aqueous hydrochloric acid

With hydrogenchloride; diethyl ether; ethanol;

upstream raw materials:

1-(4-chloro-phenyl)-2-phenyl-4-pyrrolidino-butan-2-ol

1-phenyl-3-(pyrrolidin-1-yl)propan-1-one

acetophenone

4-chlorobenzylmagnesium chloride