1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide

Base Information

• Chemical Name: 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide
• CAS No.: 64372-56-1
• Molecular Formula: C20H23FN2O2
• Molecular Weight: 342.413
• Hs Code.: 2932996560
• European Community (EC) Number: 641-954-3
• UNII: BP83XJ2B6A
• DSSTox Substance ID: DTXSID10881084
• Nikkaji Number: J2.504.709E
• Wikidata: Q27274793
• ChEMBL ID: CHEMBL3094183
• Mol file: 64372-56-1.mol

Synonyms:64372-56-1;1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide;UNII-BP83XJ2B6A;BP83XJ2B6A;CHEMBL3094183;1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carboxamide;1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide;1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarboxamide;Citalopram hydrobromide impurity A [EP];Citalopram hydrochloride impurity A [EP];(+/-)-1-(3-Dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide;1-(3-Dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide;5-Isobenzofurancarboxamide, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-;Citalopram EP Impurity A;Citalopram amide;Escitalopram EP Impurity A;SCHEMBL2869030;SCHEMBL10038948;DTXSID10881084;BDBM50494793;AKOS025401907;CS-O-07652;AC-27037;A1-06478;Q27274793;CITALOPRAM HYDROBROMIDE IMPURITY A [EP IMPURITY];CITALOPRAM HYDROCHLORIDE IMPURITY A [EP IMPURITY];1-(4-Fluorophenyl)-1-[3-(dimethylamino)propyl]-1,3-dihydroisobenzofuran-5-carboxamide;1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carboxamide;(1RS)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (Citalopram-Amide)

Chemical Property of 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide

Chemical Property:

• Melting Point: 126-128℃ (ethanol )
• Boiling Point: 444.5±45.0 °C(Predicted)
• PKA: 16.06±0.40(Predicted)
• PSA: 56.55000
• Density: 1.183±0.06 g/cm3(Predicted)
• LogP: 3.92440
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 342.17435614
• Heavy Atom Count: 25
• Complexity: 465

Purity/Quality:

98%Min ^*data from raw suppliers

1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C(=O)N)C3=CC=C(C=C3)F
• Uses: 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarboxamide, is an impurity of Citalopram (C505000), which is an inhibitor of serotonin (5-HT) uptake. It is used as an antidepressant. 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarboxamide (Escitalopram EP Impurity A), is an impurity of Citalopram (C505000), which is an inhibitor of serotonin (5-HT) uptake. It is used as an antidepressant.

Technology Process of 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide

There total 7 articles about 1-(3-Dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide 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: 95.0%

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8) → 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (64372-56-1)

Guidance literature:

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile; In dimethyl sulfoxide; for 0.5h;

With dihydrogen peroxide; In dimethyl sulfoxide; Cooling with ice; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.06.036

Reference yield: 45.0%

C20H21FNO3(1-)*Na(1+) → 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (64372-56-1)

Guidance literature:

C₂₀H₂₁FNO₃^(1-)*Na⁽¹⁺⁾; With thionyl chloride; In dichloromethane; at 4 - 25 ℃; for 0.25h;

With ammonia; In dichloromethane;

Reference yield:

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (103146-25-4,219861-18-4,481047-48-7) → 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (59729-33-8) + 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide (64372-56-1)

Guidance literature:

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile; With phosphoric acid; In water; at 105 ℃; for 14h;

With ammonia; In water; pH=8 - 10; Purification / work up;

upstream raw materials:

citalopram hydrobromide

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Downstream raw materials:

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

Refernces

• 1、 Banala, Ashwini K.,Zhang, Peng,Plenge, Per,Cyriac, George,Kopajtic, Theresa,Katz, Jonathan L.,Loland, Claus Juul,Newman, Amy Hauck. "Design and synthesis of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3- dihydroisobenzofuran-5-carbonitrile (citalopram) analogues as novel probes for the serotonin transporter S1 and S2 binding sites". . p. 9709 - 9724. Retrieved 2014/01/06.
• 2、 -. "PRODUCT". Page/Page column 10-11. . Retrieved 2008/06/13.