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

Base Information

• Chemical Name: 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide
• CAS No.: 103146-26-5
• Molecular Formula: C20H23FN2O2^.HBr
• Molecular Weight: 423.325
• Hs Code.: 2926909090
• Mol file: 103146-26-5.mol

Synonyms:Benzonitrile,4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-,monohydrobromide (9CI);

Chemical Property of 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.89E-13mmHg at 25°C
• Melting Point: 201-205 °C(lit.)
• Boiling Point: 561.6 °C at 760 mmHg
• Flash Point: 293.5 °C
• PSA: 67.49000
• LogP: 3.72548
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

CitadiolHydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Citadiol Hydrobromide is a precursor of Citalopram (C505000), an antidepressant.

Technology Process of 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide

There total 6 articles about 4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hydrobromide 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: 97.0%

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (103146-25-4,219861-18-4,481047-48-7) → 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobromide (103146-26-5)

Guidance literature:

With hydrogen bromide; at 5 - 30 ℃; for 1.5h; Temperature;

Reference yield: 76.9%

(5-cyano-3-bromomagnesio-2-(4-fluorobenzoyl)phenyl)methanol + 3-(Dimethylamino)propyl chloride (109-54-6) → 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobromide (103146-26-5)

Guidance literature:

3-(Dimethylamino)propyl chloride; With iodine; magnesium; In 2-methyltetrahydrofuran; at 60 ℃; for 4.83333h; Inert atmosphere;

(5-cyano-3-bromomagnesio-2-(4-fluorobenzoyl)phenyl)methanol; In 2-methyltetrahydrofuran; at -20 ℃; for 17.6167h; Inert atmosphere;

With hydrogen bromide; In 2-methyltetrahydrofuran; at 3 ℃; for 1h; Solvent;

Reference yield:

3-(N,N-dimethylamino)propylmagnesium chloride (19070-16-7) + 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (82104-74-3) + 4-flourophenylmagnesium bromide (352-13-6) → 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobromide (103146-26-5)

Guidance literature:

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide; In tetrahydrofuran; dichloromethane; at -5 - 5 ℃; for 0.5h;

3-(N,N-dimethylamino)propylmagnesium chloride; In tetrahydrofuran; dichloromethane; toluene; at -5 - 5 ℃;

upstream raw materials:

3-(N,N-dimethylamino)propylmagnesium chloride

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-flourophenylmagnesium bromide

3-(Dimethylamino)propyl chloride

Downstream raw materials:

citalopram hydrobromide

4-(1S)-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (+)-di-(p-toluoyl)tartaric acid

escitalopram

escitalopram oxalate

Refernces

• 1、 -. "PROCESS FOR PRODUCING HYDROBROMIDE OF DIOL COMPOUND". . . Retrieved 2020/05/14.
• 2、 -. "PREPARATION OF CITALOPRAM AND SALTS THEREOF". Page/Page column 4. . Retrieved 2010/04/30.