# US 2022/0119337 A1 · Process for preparation of halogenated benzylamine and intermediates therof

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- Number: US 2022/0119337 A1
- Document ID: US20220119337A1
- Status: Published application
- Kind: A1
- Application number: 17/422,385
- Filed: 2020-01-23
- Published: 2022-04-21
- Earliest claimed: 2019-01-25
- Assignees: SRF Limited
- Applicants: Srf Limited
- Inventors: Amardeep SINGH; Bhupender SINGH; Ram SINGH; Rajender KUMAR; Ajay Kumar CHAUDHARY; Kapil KUMAR; Anurag JAIN
- Web page: https://patentgrep.com/patent/US20220119337A1

## CPC

- C07C 209/48: by reduction of nitriles
- C07C 253/30: by reactions not involving the formation of cyano groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention provides an improved process for the preparation of halogenated benzylamine having the formula I from halogenated benzonitriles, Formula I wherein, X1 is selected from group consisting of hydrogen, chloro or fluoro, provided at least one X1 is chloro or fluoro.

## Claims

### Claim 1

A process for preparation of halogenated benzylamine of formula I,
wherein, X1 is selected from hydrogen, chloro and fluoro, provided at least one X1 is chloro or fluoro,
said process comprising the steps of:
a) selective dehalogenation of halogenated benzonitrile of formula III,
wherein, X1 is selected from hydrogen, chloro and fluoro, provided at least one X1 is chloro or fluoro; X2 is selected from chloro or bromo;
using a transition metal catalyst in presence of an alkanoic acid to obtain a halogenated benzonitrile of formula II,
wherein X1 is selected from hydrogen, chloro or fluoro, provided at least one X1 is chloro or fluoro; and
b) hydrogenating halogenated benzonitrile of formula II using hydrogenating catalyst and ammonia in presence of a solvent to obtain a halogenated benzylamine of formula I.

### Claim 2

A process for preparation of halogenated benzylamine of formula I comprising a step of hydrogenating halogenated benzonitrile of formula II being carried out by continuous addition of halogenated benzonitrile of formula II to a mixture of hydrogenating catalyst, ammonia and solvent.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein step a) is carried out using a transition metal catalyst selected from copper, zinc, and zinc/copper alloy.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein said alkanoic acid is selected from formic acid, acetic acid, and trifluoroacetic acid.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein step a) is carried out in absence of an organic solvent at a temperature of 70° C. to 90° C.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the step b) is carried out by continuous addition of halogenated benzonitrile of formula II to a mixture of hydrogenating catalyst and ammonia in presence of solvent.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein the hydrogenation is carried out using a hydrogenating catalyst selected from palladium on carbon, platinum on carbon, and Raney nickel.

### Claim 9 (depends on 1)

The process as claimed in claim 1, wherein the hydrogenation is carried out in presence of a solvent selected from 2-propanol, propanol, butanol, t-butanol, hexanol, and pentanol or mixture thereof.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein ammonia is selected from anhydrous ammonia, aqueous ammonia and alcoholic ammonia solution.