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PROCESS FOR PREPARING A CHLOROPHENYLETHYLPROPANAMINE COMPOUND

IP.com Disclosure Number: IPCOM000244501D
Publication Date: 2015-Dec-17
Document File: 3 page(s) / 65K

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The IP.com Prior Art Database

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PROCESS FOR PREPARING A CHLOROPHENYLETHYLPROPANAMINE COMPOUND


[0001] The present document discloses a process for preparing 2-chloro-N-[2-(4- chlorophenyl)ethyl]propan-1-amine hydrochloride, which is represented by Formula
(I):

Cl

Cl


· HCl (I).

NH


[0002] The process for preparing 2-chloro-N-[2-(4-chlorophenyl)ethyl]propan-1- amine hydrochloride (compound I) is depicted in the scheme below:

OH

OH

OH

Br

NH

PBr3

NH2

Cl

Cl

Cl

Cl

NH

SOCl2


· HCl

Cl


[0003] The present document discloses a process for preparing 2-chloro-N-[2-(4- chlorophenyl)ethyl]propan-1-amine hydrochloride (compound I), said process comprising:

a) reacting 2-(4-chlorophenyl)ethanol with phosphorus tribromide to obtain 2- (4-chlorophenyl)ethyl bromide;

b) reacting 2-(4-chorophenyl)ethyl bromide with 1-amino-2-propanol to obtain 1-[2-(4-chlorophenyl)ethylamino]propan-2-ol;

c) reacting 1-[2-(4-chlorophenyl)ethylamino]propan-2-ol with thionyl chloride, in toluene as solvent and in the presence of a catalytical amount of N,N- dimethylacetamide, to obtain 2-chloro-N-[2-(4-chlorophenyl)ethyl]propan-1- amine hydrochloride; and

d) optionally, recrystallizing 2-chloro-N-[2-(4-chlorophenyl)ethyl]propan-1- amine hydrochloride from a mixture of isopropanol and water.


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[0004] 2-chloro-N-[2-(4-chlorophenyl)ethyl]propan-1-amine hydrochloride (compound I) is obtained in crystalline form, which is characterized by an XRPD pattern (using (K) = 1.54056 Å radiation) having characteristic peaks at 6.7, 11.1,
13.4, 20.6, 22.2, 22.5, 24.7, 25.4, 27.1, 29.9 and 34.1º ± 0.2 degrees 2-theta, more characteristic peaks being at 6.7, 13.4, 22.2, 25.4 and 27.1º ± 0.2 degrees 2-theta, and even more characteristic peaks being at 6.7, 13.4 and 27.1º ± 0.2 degrees 2- theta. Figure 1 illustrates the XRPD pattern of 2-chloro-N-[2-(4- chlorophenyl)ethyl]propan-1-amine hydrochloride (compou...