【结 构 式】 |
【分子编号】32757 【品名】2-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetonitrile 【CA登记号】 |
【 分 子 式 】C14H20N2O2 【 分 子 量 】248.32508 【元素组成】C 67.72% H 8.12% N 11.28% O 12.89% |
合成路线1
该中间体在本合成路线中的序号:(IX)This compound has been obtained by two related ways: 1) The reaction of phenol (I) with formaldehyde gives 4-(hydroxymethyl)phenol (II), which is treated with NaCN in hot DMF to yield 2-(4-hydroxyphenyl)acetonitrile (III). The hydrolysis of (III) in refluxing ethanol/water, catalyzed by a Pt catalyst affords the corresponding acetamide (IV), which is condensed with an excess of hot epichlorohydrin (V) by means of piperidine gives 2-[4-(2-oxiranylmethoxy)phenyl]acetamide (VI). Finally, the oxirane ring of (VI) is opened with isopropylamine in methanol. 2)The condensation of acetonitrile (III) with epichlorohydrin (V) as before gives the 2-[4-(2-oxiranylmethoxy)phenyl]acetonitrile (VIII), which is treated with isopropylamine (VII) in methanol yielding 2-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetonitrile (IX). Finally, this compound is hydrolyzed with refluxing ethanol/water catalyzed by a Pt catalyst as before to afford the target acetamide.
【1】 Akisanya, J.; et al.; A synthesis of atenolol using a nitrile hydration catalyst. Org Process Res Dev 1998, 2, 4, 274. |
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) | 23540 | Phenol | 108-95-2 | C6H6O | 详情 | 详情 |
(II) | 29474 | 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol | 623-05-2 | C7H8O2 | 详情 | 详情 |
(III) | 32753 | 2-(4-hydroxyphenyl)acetonitrile; 4-Hydroxybenzyl cyanide | 14191-95-8 | C8H7NO | 详情 | 详情 |
(IV) | 32754 | p-Hydroxyphenylacetamide; 2-(4-hydroxyphenyl)acetamide; 4-Hydroxybenzeneacetamide; 4-Hydroxyphenylacetamide | 17194-82-0 | C8H9NO2 | 详情 | 详情 |
(V) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
(VI) | 32755 | 2-[4-(2-oxiranylmethoxy)phenyl]acetamide | C11H13NO3 | 详情 | 详情 | |
(VII) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
(VIII) | 32756 | 2-[4-(2-oxiranylmethoxy)phenyl]acetonitrile | C11H11NO2 | 详情 | 详情 | |
(IX) | 32757 | 2-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetonitrile | C14H20N2O2 | 详情 | 详情 |