【结 构 式】 |
【分子编号】36422 【品名】3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine 【CA登记号】 |
【 分 子 式 】C12H19NO 【 分 子 量 】193.289 【元素组成】C 74.57% H 9.91% N 7.25% O 8.28% |
合成路线1
该中间体在本合成路线中的序号:(II)The condensation of acetone (VIII) with 2-methoxybenzaldehyde (IX) by means of NaOH gives 2-methoxybenzalacetone (X), which is reduced with H2 over Raney-Ni in ethanol to yield 4-(2-methoxyphenyl)-2-butanone (XI). The Grignard reaction of (XI) with methylmagnesium iodide in ether affords 1,1-dimethyl-3-(2-methoxyphenyl) propanol (XII), which by reaction with NaCN by means of H2SO4 in acetic acid affords N-[1,1-dimethyl-3-(2-methoxyphenyl)propyl]formamide (XIII). Finally, this compound is hydrolyzed with refluxing 5N NaOH to give (II).
【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 . |
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(II) | 36422 | 3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine | C12H19NO | 详情 | 详情 | |
(VIII) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one; Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
(IX) | 12568 | 2-Methoxybenzaldehyde; o-Methoxybenzaldehyde | 135-02-4 | C8H8O2 | 详情 | 详情 |
(X) | 36418 | (E)-4-(2-methoxyphenyl)-3-buten-2-one | C11H12O2 | 详情 | 详情 | |
(XI) | 36419 | 4-(2-methoxyphenyl)-2-butanone | C11H14O2 | 详情 | 详情 | |
(XII) | 36420 | 4-(2-methoxyphenyl)-2-methyl-2-butanol | C12H18O2 | 详情 | 详情 | |
(XIII) | 36421 | 3-(2-methoxyphenyl)-1,1-dimethylpropylformamide | C13H19NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(II)The bromination of 4-benzyloxyacetophenone (VI) with Br2 in dioxane gives 4-benzyloxyphenacyl bromide (VII), which by reduction with NaBH4 in dioxane and epoxidation with NaOH water is converted into (I). The condensation of 4-benzyloxystyrene oxide (I) with 1,1-dimethyl-3-(2-methoxyphenyl)propylamine (II) in refluxing isopropanol gives 1-(4-benzyloxyphenyl)-2-[1,1-dimethyl-3-(2-methoxyphenyl)propylamino]ethanol (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.
【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 . |
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 36425 | 2-[4-(benzyloxy)phenyl]oxirane; benzyl 4-(2-oxiranyl)phenyl ether | C15H14O2 | 详情 | 详情 | |
(II) | 36422 | 3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine | C12H19NO | 详情 | 详情 | |
(III) | 36426 | 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol | C27H33NO3 | 详情 | 详情 | |
(VI) | 36423 | 1-[4-(benzyloxy)phenyl]-1-ethanone | 54696-05-8 | C15H14O2 | 详情 | 详情 |
(VII) | 36424 | 1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanone | C15H13BrO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号:(II)The oxidation of (VI) with SeO2 in hot dioxane-water gives 4-benzyloxyphenylglyoxal (IV). The condensation with (II) in refluxing ethanol, gives 4-benzyloxy-alpha-[1,1-dimethyl-3-(2-methoxyphenyl)propylimino]acetophenone (V), which is then reduced with NaBH4 in ethanol to afford (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.
【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 . |
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(II) | 36422 | 3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine | C12H19NO | 详情 | 详情 | |
(III) | 36426 | 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol | C27H33NO3 | 详情 | 详情 | |
(IV) | 31696 | 2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde | C15H12O3 | 详情 | 详情 | |
(V) | 36427 | 1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]imino]-1-ethanone | C27H29NO3 | 详情 | 详情 | |
(VI) | 36423 | 1-[4-(benzyloxy)phenyl]-1-ethanone | 54696-05-8 | C15H14O2 | 详情 | 详情 |