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【结 构 式】 
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【分子编号】12077 【品名】4-Chloro-1-[4-(1,1-dimethylethyl)phenyl]-1-butanone; 1-[4-(tert-Butyl)phenyl]-4-chloro-1-butanone; 4'-tert-Butyl-4-chlorobutyrophenone 【CA登记号】43076-61-5 |
【 分 子 式 】C14H19ClO 【 分 子 量 】238.75696 【元素组成】C 70.43% H 8.02% Cl 14.85% O 6.7% |
合成路线1
该中间体在本合成路线中的序号：(III)1) By condensation of 4-methoxybenzylamine (I) with N,N',S-trimethylisothiourea hydroiodide (C) in refluxing ethanol, followed by treatment with H2SO4.
| 【1】 Thorpe, P.; Castaner, J.; Terfenadine. Drugs Fut 1978, 3, 3, 220. |
| 【2】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); 1-Aroylalkyl-4-diphenylmethyl piperidines. DE 2303305; ES 410730; FR 2181692; GB 1412605; JP 48085576; US 3806526 . |
| 【3】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); Olefinic 4-substituted piperidino deriatives. ES 410732; FR 2181689; GB 1413140; JP 48085579; US 3862173 . |
| 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) | 17179 | 2-[4-(4-[4-[hydroxy(diphenyl)methyl]-1-piperidinyl]butanoyl)phenyl]-2-methylpropyl acetate | 76811-96-6 | C34H41NO4 | 详情 | 详情 |
| (III) | 12077 | 4-Chloro-1-[4-(1,1-dimethylethyl)phenyl]-1-butanone; 1-[4-(tert-Butyl)phenyl]-4-chloro-1-butanone; 4'-tert-Butyl-4-chlorobutyrophenone | 43076-61-5 | C14H19ClO | 详情 | 详情 |
| (IV) | 39797 | 1-[4-(tert-butyl)phenyl]-4-[4-[hydroxy(diphenyl)methyl]-1-piperidinyl]-1-butanone | C32H39NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)This compound can be obtained by two related routes: 1) Condensation of 4-hydroxypiperidine (I) with p-tert-butyl-omega-chlorobutyrophenone (II) in hot methyl isobutyl ketone in presence of sodium bicarbonate gives 1-[3-(4-tert-butylbenzoyl)propyl]-4-hydroxypiperidine (III), which reacts with diphenylmethyl bromide (IV) in methyl isobutyl ketone to give ebastine. 2) 4-Diphenylmethoxypiperidine (VI), obtained by alkaline hydrolysis of 1-ethoxycarbonyl-4-diphenyl-methoxypiperidine (V) was reacted with p-tert-butyl-omega-chlorobutyrophenone (II) to give ebastine.
| 【1】 Spickett, R.G.W.; Moragues, J.; Prieto, J.; Vega, A. (Fordonal S.A.); Piperidine derivs. EP 0134124B; US 4550116 . |
| 【2】 Moragues, J.; Roberts, D.J.; EBASTINE. Drugs Fut 1990, 15, 7, 674. |
| 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) | 12076 | 4-Piperidinol; 4-Hydroxypiperidine | 5382-16-1 | C5H11NO | 详情 | 详情 |
| (II) | 12077 | 4-Chloro-1-[4-(1,1-dimethylethyl)phenyl]-1-butanone; 1-[4-(tert-Butyl)phenyl]-4-chloro-1-butanone; 4'-tert-Butyl-4-chlorobutyrophenone | 43076-61-5 | C14H19ClO | 详情 | 详情 |
| (III) | 12078 | 1-[4-(tert-Butyl)phenyl]-4-(4-hydroxypiperidino)-1-butanone | C19H29NO2 | 详情 | 详情 | |
| (IV) | 12079 | Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide | 776-74-9 | C13H11Br | 详情 | 详情 |
| (V) | 12080 | ethyl 4-(benzhydryloxy)tetrahydro-1(2H)-pyridinecarboxylate | C21H25NO3 | 详情 | 详情 | |
| (VI) | 12081 | 4-(Benzhydryloxy)piperidine; Benzhydryl 4-piperidinyl ether | C18H21NO | 详情 | 详情 |