Process for preparing

1. A process for preparing a N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl) propylamine compound of formula (III),

comprising reacting a (S)-methylhydroxylaminopropanol compound of formula (II)

with KOR 1 and halonaphthalene in DMSO,

wherein R is a hydrogen atom, C 1-8 alkyl or C 6-10 aryl; R 1 is tert-butyl;

and halo is F, Cl, Br or I.

2. The process of claim 1 , wherein R is C 1-4 alkyl.

3. The process of claim 2 , wherein R is methyl.

4. The process of claim 1 , wherein an amount of the halonaphthalene ranges from 1.5 to 7.0 equivalents based on 1.1 equivalent of the KOR 1 .

5. The process of claim 1 , wherein the process is carried out at a temperature ranged from 10° C. to 110° C.

6. A process for preparing (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine, comprising steps of:

(i) performing a Marmich reaction of 2-acetylthiophene, formaldehyde and a methylhydroxylamine compound of formula, HNCH 3 (OR), to form a substituted amino ketone of formula (I),

(ii) reducing the substituted amino ketone of formula (I) enatioselectively to a (S)-methylhydroxylaminopropanol compound of formula (II),

(iii) reacting the (S)-methylhydroxylaminopropanol compound of formula (II) with KOR 1 and halonaphthalene in DMSO to form a N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound of formula (III),

(iv) performing an N,O-cleavage reaction of the N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound of formula (III) to form (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine,

wherein R is a hydrogen atom, C 1-8 alkyl or C 6-10 aryl; R 1 is C 1-6 alkyl; and halo is F, Cl, Br or I.

7. The process of claim 6 , wherein R is C 1-4 alkyl.

8. The process of claim 7 , wherein R is methyl.

9. The process of claim 6 , wherein R 1 is butyl.

10. The process of claim 6 , wherein an amount of the halonaphthalene ranges from 1.5 to 7.0 equivalents based on 1.1 equivalent of the KOR 1 .

11. The process of claim 6 , wherein the substituted amino ketone of formula (I) obtained in the step (i) is a free form or an acid addition salt.

12. The process of claim 6 , wherein the step (ii) is performed by chiral reduction, allowing the (S)-methylhydroxylaminopropanol compound of formula (II) to be in an optically active form.

13. The process of claim 12 , wherein a chiral reducing agent used in the chiral reduction is selected from the group consisting of complex hydride, borane, transition metal catalyst and microbial dehydrogenase.

14. The process of claim 13 , wherein a reduction catalyst comprising an enantiomer-enriched bidentate phosphorus-containing ligand, a transition metal and a diamine is used, and wherein the diamine is a chiral diamine.

15. The process of claim 6 , wherein the reaction in the step (iii) is carried out at a temperature ranged from 10° C. to 110° C.

16. The process of claim 6 , wherein the N,O-cleavage reaction of the N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound of formula (III) in the step (iv) is carried out by hydrogenation in an alcohol in the presence of Raney-nickel at a temperature ranged from 15° C. to 80° C.

17. The process of claim 6 , wherein the N,O-cleavage reaction of the N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound of formula (III) in the step (iv) is carried out by a chemical reduction using LiAlH 4 or zinc metal as a reducing agent.

18. The process of claim 6 , wherein the step (i) is performed at a temperature ranged from 15° C. to 90° C.

19. The process of claim 6 , wherein the step (ii) is performed at a pH value ranged from 6 to 14.