FI60554B - FOER REFRIGERATION FOR NAMINOALKYL SUBSTITUTES - Google Patents

Description

E5sF * l [B] (11) advertisement publication 50554 LJ 1 'UTLÄGGN I NGSSKRIFT OU Ό ° ** C (45) Patentti oyjn.v. ., iy 10 1; -

Patent roeddelat v (51) Kv.lk?/lnt.CI.3 C 07 C 103/82 FINLAND —FINLAND (21) P * t * nttlh »k * mu * - PatMMansBknlng 33 ^ 1/73 (22) HakamlapIWI - An * »knlngtd« g 29.10.73 ^ '(23) Alkupilvi - Giltlghattdag 29.10.73 (41) Tullut | ulkl «akal - Bllvlt offantllg 01.05. lk

National Board of Patents and Registration .... Μϊ ... ... ,, Β. . . , ^. (44) Date of issue and date of issue. - 00 ΊΛ

Patent and registration authorities Antkkan utlagd och utUkriftan publicarad 30.10. Ö1 (32) (33) (31) Catch requested —Begird prloritet 31.10. 72

Japan-Japan (JP) 109721/72 (71) Societe d'fitudes Scientifiques et Industrielles de 1'Ile-de-France, U6 boulevard de Labor-Maubourg, 75 Paris 7 °, France-Frankrike (FR) (72) Akira Morimoto, 0saka-fu, Hisashi Takasugi, Osaka-shi, Japan i-Japan (JP) (7M Oy Kolster Ab (5 * 0 Process for the preparation of N-aminoalkyl-substituted benzamides)

The invention relates to a new process for the preparation of N-aminoalkyl-substituted benzamides.

The invention is characterized in that the N-aminoalkyl-substituted benzamide of the general formula is / R 1 CONH-W-N.

ί * 2 (I) wherein W is an alkylene group having 1 to 3 carbon atoms, R 1, R 2 and R 2 represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is an amino group protected by an unsubstituted or substituted benzyl group, and X or. hydrogen or a halogen atom, or a salt thereof, is reduced to give an N-aminoalkyl-substituted benzamide or a salt thereof having the general formula or.

2 60554 In CONH-W-N (II) A'-nh2; 'V, R1, R1 and X have the same meaning as above.

It is known from GB patent publication 99-023 to prepare substituted k-aminobenzamides. In the preparation of N- (diethylaminoethyl) -2-methoxy-14-amino-5-chlorobenzamide by this known method by hydrolysis, the corresponding U-acetaminobenzamide has a yield of%. The advantage of the process according to the invention over the known process is that : using the corresponding it-benzylaminobenzaride as starting material, the yield of N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide is 86.7%> benzamide or a reactive derivative thereof containing a functional group in a carboxyl group to react with the corresponding diamine or a salt thereof. The reaction of the present invention is carried out by reducing the N-araminoalkyl-substituted benzamide (II) or a salt thereof. In the starting material of formula (i), the alkylene group W includes, for example, ethylene and propylene. As the alkyl group R2 or R1, for example, methyl, ethyl and propyl groups can be mentioned. Examples of the amino group R 1 include benzylamino, nitrobenzylamino, and methoxybenzylamino. As the halogen, chlorine, bromine, iodine and fluorine can be mentioned. As the salt of the starting material (I), there can be mentioned salts of mineral acids such as hydrochlorides and sulfates and salts of organic acids such as acetates, tartrates and maleates.

In the reaction of this invention, the reduction of the starting material (I) with hydrogen in the presence of a metal catalyst for catalytic reduction such as palladium, carbon, Raney nickel or platinum oxide is most often used as the reduction method. It is preferred to carry out the reaction using the starting material (I) in the form of a salt in the presence of an acid such as an organic acid, for example acetic acid or propionic acid, or a mineral acid, for example hydrochloric acid or sulfuric acid. The reaction is usually carried out in a solvent, and any solvent such as raethanol, ethanol, isopropanol, butanol, tetrahydrofuran and dioxane which does not participate in the reaction can be used. These solvents may be used alone or as a mixture of two or more solvents.

The product (II) thus obtained can be converted into a salt of a mineral acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, etc. or an organic acid such as oxalic acid, tartaric acid, maleic acid, picric acid and the like by conventional methods.

The invention is now described in the following example.

Example 0.1 g of 10- to 10-palladium-carbon was added to a solution of 0.1 g of N- (2-diethylaminoethyl) -2-methoxy-U-benzylamino-5-chlorobenzamide hydrochloride dissolved in 300 ml of 99- ethanol, and the catalytic reaction was carried out in vc-base stream at normal pressure. After about 28 ml of hydrogen was absorbed, the reduction was stopped and the catalyst was removed from the reaction mixture by filtration. Guodos concentrated under reduced pressure and the residue was dissolved in 20 ml of water. The pH of the resulting solution was adjusted to 9, and the precipitated white crystals were collected by filtration, washed with water, and dried to give 0.28 g of N- (2-diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide (yield 86.7%). , which melted at a temperature of 1U? ~ 1UU ° C.

By uniform methods, the following compounds were obtained: N-aminoethyl-2-methoxy-U-amino-5-chlorobenzamide (m.p. 150-153 ° C) and N- (2-diethylaminoethyl) -2-methoxy-1'-aminobenzamide (yellow sticky pasta).

Claims (1)

A process for the preparation of N-aminoalkyl-substituted benzamides of the general formula CONH-WN I S2 ^ Γ ° * 3 (II) NH2 wherein W is an alkylene group having 1 to 3 carbon atoms, 1, Rg and R represent a hydrogen atom or Alkyl group having 1 to 3 carbon atoms and X is hydrogen or a halogen atom, or for the preparation of their salts, characterized in that the N-aminoalkyl-substituted benzamide of the general formula (I) CONH-WN Ϊ rVOR3 I (I) x ^ Y Rk wherein W, R1, R2, and X are as defined above and R1 is an amino group protected by an unsubstituted or substituted benzyl group or a salt thereof is reduced.