Process for the manufacture of 4-aminobenzoamidine dihydrochloride

Patent metadata

Field	Value
Publication number	US-10040750-B2
Application number	US-201615190756-A
Country	US
Kind code	B2
Filing date	Jun 23, 2016
Priority date	Oct 22, 2012
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

The present invention relates to a process for the preparation of 4-aminobenzoamidine (4-AMBA) salts of general formula (I)

preferably the salts thereof with hydrochloric or hydrobromic acid, particularly preferred the dichloride salt.

First claim

We claim:

1. A process for the preparation of a compound of formula (II), wherein the process comprises reaction step (A):
in step (A) treating 4-aminobenzonitril (III) with HX in a pure or mixed alcoholic solvent at a reaction pressure of about 0 to 10 atm,

to form compound (II)

wherein R is methyl, ethyl, propyl, or butyl, and X is Cl or Br,
with the provisio that wherein if R is ethyl, the reaction pressure is between 2 to 6 atm.

2. The process for the preparation of a compound of formula (II) according to claim 1 , wherein the alcoholic solvent or alcoholic solution is ethanolic or methanolic.

3. The process for the preparation of a compound of formula (II) according to claim 1 , wherein the alcoholic solvent or alcoholic solution is methanolic.

4. The process according to claim 1 , wherein the HCl or HBr in step (A) is in a concentration from 5% to 30% (weight %) in alcohol.

5. The process according to claim 1 , wherein a molar ratio of HCl or HBr to compound (III) is from 2:1 to 20:1.

6. The process according to claim 1 wherein the reaction according to step (A) is conducted at a temperature from −10 ° C. to 80 ° C.

Assignees

• Boehringer Ingelheim Int

Inventors

• Dong Weitong
• Hemp Christian Wolfgang
• Jin Xiangle
• Lu Jun
• Scholz Ulrich
• Su Shengmin
• Xu Wei
• Yang Jinsong

Classifications

• C07C213/00 Primary

  Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton · CPC title

• C07C257/18

  having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C217/76

  having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton · CPC title

• C07C257/08 Primary

  having carbon atoms of imino-carboxyl groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C249/02

  of compounds containing imino groups · CPC title