# US 9,040,751 B2 · Method for producing ring-halogenated N,N-dialkylbenzylamines

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- Number: US 9,040,751 B2
- Document ID: US9040751B2
- Status: Granted
- Kind: B2
- Application number: 14/236,163
- Filed: 2012-08-01
- Published: 2014-08-07
- Granted: 2015-05-26
- Earliest claimed: 2011-08-04
- Assignees: LANXESS Deutschland GmbH
- Applicants: Jordan Hartwig
- Inventors: Jordan Hartwig
- Web page: https://patentgrep.com/patent/US9040751B2

## CPC

- C07C 209/10: with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
- C07C 209/08: with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C 221/00: Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to a method for preparing ring-halogenated N,N-dialkylbenzylamines and intermediates obtainable therefrom for preparing agrochemicals and pharmaceutically active ingredients.

## Claims

### Claim 1

A method for preparing compounds of the formula (I)
in which
n is 0, 1, 2 or 3
the residues R1 are each independently a halogen atom bonded to the aromatic ring,
the residues R2 are each independently C1-C8-alkyl, C6-C12-aryl or C7-C13-arylalkyl or both residues R2 together are a straight-chain or branched C3-C12-alkylene residue, which may optionally be interspersed by one or more oxygen atoms,
the method comprising reacting compounds of the formula (II)
with compounds of the formula (III)
HN(R2)2
where the residues R1 and R2 in the formulae (III) and (II) have the meanings stated under the formula (I), and
X is chlorine, bromine, iodine, —OSO2—(C1-C6-alkyl) or —OSO2—(C1-C6-perfluoroalkyl)
wherein:
the molar ratio of compounds of the formula (III) to compounds of the formula (II) is 3:1 to 50:1;
organic solvent is optionally used in an amount of 0% to 10% by weight, based on the sum of compounds of the formulae (II) and (III) used;
water is used in the reaction in an amount of more than 10% by weight based on the amount of compound of the formula (II) used; and
the reaction is conducted at a temperature of 90° C. to 180° C.

### Claim 2 (depends on 1)

The method as claimed in claim 1, wherein the method is a method for 2-chloro-N,N-dimethylbenzylamine by reacting 2-chlorobenzyl chloride with dimethylamine.

### Claim 3 (depends on 1)

The method as claimed in claim 1 wherein:
the reaction temperature is 130 to 150° C.;
the reaction is conducted at a pressure of 5 to 35 bar;
n is 1, and R1 and X are chlorine;
the molar ratio of compounds of the formula (III) to compounds of the formula (II) is 5:1 to 20:1;
no organic solvent is used; and
the amount of water used 100 to 1000%, by weight, based on the amount of compound of formula (II) used.

### Claim 4 (depends on 1, 2, 3)

The method as claimed in any one of claims 1 to 3, further comprising conducting the reaction at a pressure of 2 to 300 bar.

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein the method comprises conducting the reaction continuously.

### Claim 6 (depends on 1)

The method for preparing compounds of the formula (I) as claimed in claim 1, wherein the prepared compounds of formula (I) after the method of claim 1 are in a mixture having a residual content of compounds of the formula (IV)
in which R1 has the meaning stated in claim 1
of 0.050 to 2.0% by weight and the method further comprises contacting the mixture with an alkali metal borohydride or an alkali metal aluminum hydride to react with the compounds of formula (IV); and subsequently separating compounds of formula (I) from the reacted compounds of formula (IV) by distillation.

### Claim 7 (depends on 6)

The method as claimed in claim 6, wherein the method is a method for preparing 2-chloro-N,N-dimethylbenzylamine and the residual compound is 2-chlorobenzaldehyde.

### Claim 8 (depends on 6, 7)

The method as claimed in claim 6 or 7, wherein the alkali metal borohydride is sodium borohydride.

### Claim 9 (depends on 1, 6)

The method as claimed in claim 6, wherein the method of claim 6 is carried out subsequent to the method as claimed in claim 1.

### Claim 10 (depends on 1)

A method for preparing compounds of the formula (V)
in which the residues R2 are each independently C1-C8-alkyl, C6-C12-aryl or C7-C13-arylalkyl or both residues R2 to together are a straight-chain or branched C3-C12-alkylene residue, which may optionally be interspersed by one or more oxygen atoms,
and R3 is C1-C6-alkyl, C1-C8-alkoxy, C6-C12-aryl or C7-C13-arylalkyl,
the method comprising preparation of compounds of the formula (I) according to claim 1; reacting compounds of the formula (I), with an alkali metal or alkaline earth metal or a compound of the type M(C1-C6-alkyl) where M is an alkali metal, and subsequently with compounds of the formula (VI)
in which the residue R3 has the meaning stated for formula (V) and
R4 is C1-C8-alkyl, C6-C12-aryl or C7-C13-arylalkyl.