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

• 174458-41-4 1-[4-(p-fluorobenzyl)-2-morpholinylmethyl]-3-methylurea 
• 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 

Relevant articles and documents

Citric acid mosapride intermediate product and application

The invention belongs to the field of medical chemistry synthesis, and provides a preparation method of citric acid mosapride intermediate product IV 4-[(4-fluorophenyl)methyl]-2-morpholinemethanaminesalt and citric acid mosapride. The 2-(4-fluorobenzoamido)ethanol and 1H-Isoindole-1,3(2H)-dione,2-(2-oxiranylmethyl) are taken as raw materials, and the intermediate product IV 4-[(4-fluorophenyl)methyl]-2-morpholinemethanamine salt is obtained after acid treating is conducted; the intermediate product IV and an intermediate V 2-oxethyl-4-acetamido-5-Chlorobenzoic acid ethyl ester compounds aretaken as raw materials, dichloromethane is taken as a solvent, and EDCI and DMAP are taken as catalysts to prepare mosapride salt; the mosapride salt is reacted with citric acid aqueous solution to prepare citric acid mosapride. The intermediate product has the advantages that products are high in yield, raw materials are easy to obtain, the production cost is low, and the intermediate product issuitable for industrialized production.

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