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              藥物詳細合成路線

              Name Moclobemide;Ro-11-1163;Moclamine;Manerix;Aurorix
              Chemical Name 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide
              CAS 71320-77-9
              Related CAS
              Formula C13H17ClN2O2
              Structure
              Formula Weight 268.74564
              Stage 上市-1990
              Company Roche (Originator), Dainippon Pharmaceutical (Licensee)
              Activity/Mechanism Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, Social Phobia, Treatment for, MAO-A Inhibitors
              Syn. Route 1
              Route 1
              this compound can be prepared in several different ways:1) by reaction of p-chlorobenzoyl chloride (i) with n-(2-aminoethyl)morpholine (ii) in pyridine.2) by reaction of p-chlorobenzoyl anhydride (iii) with n-(2-aminoethyl)morpholine (ii) in pyridine.3) by reaction of methyl p-chlorobenzoate (iv) with n-(2-aminoethyl)morpholine (ii) at 120 c.4) by reaction of n-(p-chlorobenzoyl)succinimide (v) with n-(2-aminoethyl)morpholine (ii) in dioxane.5) by reaction of p-nitrophenyl p-chlorobenzoate (vi) with n-(2-aminoethyl)morpholine (ii) in thf.6) by reaction of p-chloro-n-(2-chloroethyl)benzamide (vii) with morpholine (viii) at 100 c.7) by reaction of p-chlorobenzoylaziridine (ix) with morpholine (viii) in refluxing toluene.8) by reaction of p-chlorobenzaldehyde (x) with n-(2-aminoethyl)morpholine (ii) in refluxing benzene to give 4-[2-[(p-chlorobenzylidene)amino]ethyl]morpholine (xi), followed by an oxidation with h2o2 in methanol.9) by reaction of p-chloro-n-(2-morpholinoethyl)thiobenzamide (xii) with lead tetraacetate in refluxing water.11) by reaction of p-chlorobenzoic acid (xiv) with n-(2-aminoethyl)morpholine (ii) by means of dicyclohexylcarbodiimide in pyridine, or by means of chloroformic acid ethyl ester and triethylamine in acetone.10) by isomerization of (alpha-(p-chlorophenyl)-n-(2-morpholinoethyl)nitrone (xiii) in hot acetic acid - acetic anhydride, followed by a treatment with naoh.
              List of intermediates No.
              [(1s)-2-bromo-2-(bromomethyl)cyclopropyl]methyl acetate (i)
              2-(4-benzhydryl-1-piperazinyl)ethyl (z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate (viii)
              4-amino-5-ethyl-4h-1,2,4-triazol-3-ylhydrosulfide; 4-amino-5-ethyl-4h-1,2,4-triazole-3-thiol (ii)
              methyl 5-acetyl-2-[(2-oxotetrahydro-3-furanyl)oxy]benzoate (xiv)
              n-(2-ethoxybenzyl)[3-(4-methylphenoxy)phenyl]methanamine; n-(2-ethoxybenzyl)-n-[3-(4-methylphenoxy)benzyl]amine (x)
              (3s,6r,7r,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoic acid (iii)
              (3s,6s,7r,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoic acid (iv)
              (1e,3s)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol (v)
              (1s)-1-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl (3s,6s,7s,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoate (vi)
              (1s)-1-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl (3s,6s,7r,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoate (vii)
              (1s)-1-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl (3s,6r,7r,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoate (ix)
              (1s)-1-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl (3s,6r,7s,8s,12z)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-16-methoxy-4,4,6,8-tetramethyl-5-oxo-12-hexadecenoate (xi)
              (4s,7r,8s,9s,16s)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-hydroxy-5,5,7,9-tetramethyl-16-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxa-13-cyclohexadecene-2,6-dione (xii)
              3-methyl-3-(trifluoromethyl)-1,2-dioxirane (xiii)
              Reference 1:
                  bukard, w.; wyss, p.c. (f. hoffmann-la roche ag); benzamides. be 0851422; ca 1076112; de 2706179; fr 2340940; gb 1512194; jp 52100476; nl 7701144; us 4210754; za 7700488 .
              Reference 2:
                  blancafort, p.; serradell, m.n.; castaner, j.; grau, m.; moclobemide. drugs fut 1983, 8, 2, 124.

              來源:藥化網

              作者:藥化小編

              摘要:本文合成路線介紹的是藥物中文名嗎氯貝胺;英文名Moclobemide;Ro-11-1163;Moclamine;Manerix;Aurorix;CAS[71320-77-9]

               
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