【结 构 式】 |
【分子编号】29580 【品名】N-(2-[4-[benzyl(methyl)amino]-2-fluorophenyl]-1-methylethyl)-2-chloroacetamide 【CA登记号】 |
【 分 子 式 】C19H22ClFN2O 【 分 子 量 】348.8476632 【元素组成】C 65.42% H 6.36% Cl 10.16% F 5.45% N 8.03% O 4.59% |
合成路线1
该中间体在本合成路线中的序号:(VIII)Reaction of 3-fluoroaniline (I) with formic acid gave formanilide (II), which was reduced by means of LiAlH4 to afford 3-fluoro-N-methylaniline (III). Further alkylation of (III) with benzyl chloride provided the tertiary amine (IV). Vilsmeier-Haack formylation of (IV) with POCl3 and DMF yielded aldehyde (V), which was condensed with nitroethane in the presence of ammonium acetate to give the 2-nitropropene derivative (VI). After reduction of (VI) to the amine (VII) with LiAlH4, condensation with chloroacetyl chloride afforded chloracetamide (VIII). Subsequent displacement of the chlorine of (VIII) with dibenzylamine yielded the tertiary amine (IX). Finally, hydrogenolytic debenzylation of (IX) in the presence of Pd/C furnished the title compound.
【1】 Larsson, L.-G.; Florvall, L.; Ross, S.B.; Fagervall, I.; Prodrugs of neuron-selective monoamine oxidase inhibitors: Amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes. Eur J Med Chem 1999, 34, 2, 137. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 | |
12117 | Nitroethane; 1-Nitroethane | 79-24-3 | C2H5NO2 | 详情 | 详情 | |
19171 | 1-(Chloromethyl)benzene; Benzyl chloride | 100-44-7 | C7H7Cl | 详情 | 详情 | |
(I) | 20697 | 3-fluoroaniline; 3-fluorophenylamine | 372-19-0 | C6H6FN | 详情 | 详情 |
(II) | 29575 | 3-fluorophenylformamide | C7H6FNO | 详情 | 详情 | |
(III) | 20700 | 3-fluoro-N-methylaniline; N-(3-fluorophenyl)-N-methylamine | C7H8FN | 详情 | 详情 | |
(IV) | 29576 | N-benzyl-3-fluoro-N-methylaniline; N-benzyl-N-(3-fluorophenyl)-N-methylamine | C14H14FN | 详情 | 详情 | |
(V) | 29577 | 4-[benzyl(methyl)amino]-2-fluorobenzaldehyde | C15H14FNO | 详情 | 详情 | |
(VI) | 29578 | N-benzyl-N-[3-fluoro-4-[(E)-2-nitro-1-propenyl]phenyl]-N-methylamine; N-benzyl-3-fluoro-N-methyl-4-[(E)-2-nitro-1-propenyl]aniline | C17H17FN2O2 | 详情 | 详情 | |
(VII) | 29579 | N-[4-(2-aminopropyl)-3-fluorophenyl]-N-benzyl-N-methylamine; 4-(2-aminopropyl)-N-benzyl-3-fluoro-N-methylaniline | C17H21FN2 | 详情 | 详情 | |
(VIII) | 29580 | N-(2-[4-[benzyl(methyl)amino]-2-fluorophenyl]-1-methylethyl)-2-chloroacetamide | C19H22ClFN2O | 详情 | 详情 | |
(IX) | 29581 | N-(2-[4-[benzyl(methyl)amino]-2-fluorophenyl]-1-methylethyl)-2-(dibenzylamino)acetamide | C33H36FN3O | 详情 | 详情 |