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Crystalline form of N-(3-methoxyphenyl)cinnamamide

IP.com Disclosure Number: IPCOM000249235D
Publication Date: 2017-Feb-12
Document File: 2 page(s) / 370K

Publishing Venue

The IP.com Prior Art Database

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This is the abbreviated version, containing approximately 93% of the total text.

Crystalline form of N-(3-methoxyphenyl)cinnamamide

N-(3-methoxyphenyl)cinnamamide (referred to as Compound III) has the following

structure:

Compound III is obtained by a process as shown in the scheme below:

The synthesis of compound III involves a reaction between m-Anisidine (referred to

as Compound I) and Cinnamoyl Chloride (referred to as Compound II). The

isolation of the product by filtration gives N-(3-methoxyphenyl)cinnamamide

(referred to as Compound III).

Preparation of N-(3-methoxyphenyl)cinnamamide [Compound III]

A 50mL round flask was loaded with Compound I (1g, 0.008 mol), Na2CO3 (2.58g, 0.024

mol) and acetone (20mL). The obtained slurry was cooled to 0 ° C by an ice/water bath. Next,

Compound II (1.35g, 0.0081mol) was added to the slurry and the reaction mixture was

warmed to 40 °

C for 1h, almost until full consumption (LT-2%) of Compound I was

obtained. The reaction mixture was filtrated under vacuum and washed with acetone. The

filtrate was evaporated followed by dissolving in acetone (10mL) at 40 °

C. Water (10mL)

was added drop-wise upon this temperature to give precipitation. The obtained product was

isolated by vacuum filtration, washed with H2O (10mL) and dried in vacuum oven at 50 ° C

for about 18 h to give 1.49 g of N-(3-methoxyphenyl)cinnamamide (Compound III) as

a brown crystalline solid with 96.63% purity.

The obtained crystalline solid was characterized by XRPD. The XRPD pattern is

presented in the following figure:

Main XRD peak positions of cr...