Atenolol, ICI-66082, Blokium, Tenormin

阿替洛尔Chemical Name: 2-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide
CAS No. 29122-68-7
项目整合开发状态: Launched-1975
项目研究机构: Pfizer (Proprietary), AstraZeneca (Originator), Almirall Prodesfarma (Licensee)
合成路线: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.