112914-13-3

Basic information

• Product Name: 4-[(4-Fluorophenyl)methyl]-2-morpholinemethanamine
• Synonyms: C-[4-(4-FLUORO-BENZYL)-MORPHOLIN-2-YL]-METHYLAMINE DIHYDROCHLORIDE;2-Aminoethy-4-(4-Fluorobenzyl)-morpholine;2-(AminoMethyl)-4-(4-FluoroBenzyl)Morpholine,Mosapride;2-Aminomethy-4-(4-fluorobenzyl)morpholine;4-[(4-Fluorophenyl)methyl]-2-morpholinemethanamine;{4-[(4-fluorophenyl)Methyl]Morpholin-2-yl}MethanaMine;(4-(4-Fluorobenzyl)Morpholin-2-yl)MethanaMine;2-(Aminomethyl)-4-(4-fluorobenzyl)morpholine, 1-{[2-(Aminomethyl)morpholin-4-yl]methyl}-4-fluorobenzene
• CAS NO: 112914-13-3
• Molecular Formula: C₁₂H₁₇FN₂O
• Molecular Weight: 224.28
• Product Categories: Pharmaceutical Intermediates;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 112914-13-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 317.439 °C at 760 mmHg
• Flash Point: 145.782 °C
• Appearance: /
• Density: 1.145 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Refrigerator
• PKA: 9.37±0.29(Predicted)
• CAS DataBase Reference: 4-[(4-Fluorophenyl)methyl]-2-morpholinemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4-Fluorophenyl)methyl]-2-morpholinemethanamine(112914-13-3)
• EPA Substance Registry System: 4-[(4-Fluorophenyl)methyl]-2-morpholinemethanamine(112914-13-3)

Safety Data

• Hazardous Substances Data: 112914-13-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear Pale Yellow Oil

Uses

Mosapride intermediate.

InChI:InChI=1/C12H17FN2O/c13-11-3-1-10(2-4-11)8-15-5-6-16-12(7-14)9-15/h1-4,12H,5-9,14H2

Upstream product

• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 22116-33-2 2-(4-fluoro-benzyl-amino)-ethanol 
• 636582-78-0 2-[4-(4-fluoro-benzyl)-morpholine-2-yl-methyl]-isoindole-1,3-dion 
• 131322-23-1 <2-(acetylamino)methyl>morpholine acetyl salt 
• 112913-96-9 2-(N-acetylaminomethyl)-4-benzylmorpholine 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 112913-94-7 2-<(acetylamino)methyl>-4-(4-fluorobenzyl)morpholine 

Downstream Products

• 112885-41-3 mosapride 
• 112885-42-4 mosapride citrate 
• 112885-34-4 4-acetylamino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide 
• 1420999-21-8 2-[(1-benzylpiperidin-4-yl)amino]-N-{[4-(4-fluorobenzyl)morpholin-2-yl]methyl}nicotinamide 
• 174458-41-4 1-[4-(p-fluorobenzyl)-2-morpholinylmethyl]-3-methylurea 

Relevant articles and documents

Method for preparing mosapride citrate intermediate

The invention belongs to the technical field of medicines and particularly relates to a method for preparing a mosapride citrate intermediate IV 4-(4-fluorophenyl)-2-aminomethyl morpholine. The methodcomprises the following steps: phthalimide potassium salt and dichloro-2-propanol react to produce an intermediate II N-(2-hydroxy-3-chloropropyl) phthalimide, then the produced intermediate II and an intermediate I 2-(4-fluorphenylamine)ethyl alcohol are condensed to prepare an intermediate III N-3-[4-fluorophenyl-2-(hydroxy-ethylamine)-2-hydroxypropyl]phthalic diamide, and the intermediate IIIis subjected to cyclization and hydrolysis to obtain the intermediate IV 4-(4-fluorophenyl)-2-aminomethyl morpholine. The method is short in route, lower in production cost and suitable for industrialproduction.

PROCESS FOR THE SYNTHESIS OF A BENZAMIDE DERIVATIVE

The invention relates to a process for the synthesis of mosapride citrate of formula (I), the chemical name: (R,S)-4-amino-5-chloro-2-ethoxy-N-{ [4-(4-fluoro-benzyl)-2- morpholinyl]-methyl}benzamide citrate dihydrate, (I), (II) reacting the compound of formula (II) with di-tert-butyl-dicarbonate in an alcohol in the presence of a base, the obtained product is ethylated in an inert solvent in the presence of a base, the obtained compound is hydrolyzed with an alkyl-hydroxide and the obtained salt neutralized with an acid, the obtained product is chlorinated, and the obtained compound of formula (VI) is reacted with the compound of formula (VII), (VI), (VII) where BOC is tert-butoxy-carbonyl protecting group and removing the protecting group from the obtained compound of formula (VIII) the mosapride base is prepared, (VIII) where BOC is defined as above and in desired case with an acid, preferably with citric acid a pharmaceutically acceptable salt, preferably the mosapride citrate dehydrate of formula (I) is produced.

Synthesis and biological activity of 4-amino-5-chloro-2-ethoxy-3- hydroxybenzamides, metabolites of a new gastroprokinetic agent, mosapride

To confirm the proposed structures of the minor metabolites of a potential gastroprokinetic agent, mosapride, 4-amino-5-chloro-2-ethoxy-3- hydroxy-N-(2-morpholinylmethyl)benzamide (3) and the N-(5-oxo-2- morpholinyl)methyl analogue 4 were prepared. As the