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【结 构 式】 
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【分子编号】51928 【品名】4-[allyl(isopropyl)amino]-2-(2-chlorophenyl)-2-[2-(1-piperidinyl)ethyl]butanenitrile 【CA登记号】 |
【 分 子 式 】C23H34ClN3 【 分 子 量 】387.99588 【元素组成】C 71.2% H 8.83% Cl 9.14% N 10.83% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of N-isopropylethanolamine (I) with allyl bromide (II) in THF gives the secondary amine (III), which is treated with SOCl2 in dichloromethane to yield the chloroethylamine (IV). The condensation of (IV) with 2-(2-chlorophenyl)-4-(1-piperidinyl)butyronitrile (V) by means of KOH in DMSO affords the adduct (VI), whose nitrile group is hydrolyzed with H2SO4 to provide the corresponding amide (VII). The elimination of the allyl group of (VII) by means of a Rh catalyst and 1,4-diazabicyclo[2,2,2]octane (DABCO) in refluxing aqueous ethanol gives the secondary amine (VIII), which is finally acetylated with Ac2O in ethyl acetate to yield the target diamide.
| 【1】 Awasthi, A.K.; Paul, K.; A new and improved synthesis of bidisomide. Org Process Res Dev 2001, 5, 5, 528. |
| 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) | 51925 | 2-(Isopropylamino)ethanol; 2-(iso-Propylamino)ethanol; N-Isopropylethanolamine | 109-56-8 | C5H13NO | 详情 | 详情 |
| (II) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (III) | 51926 | 2-[allyl(isopropyl)amino]-1-ethanol | C8H17NO | 详情 | 详情 | |
| (IV) | 51927 | N-(2-chloroethyl)-N-isopropyl-2-propen-1-amine; N-allyl-N-(2-chloroethyl)-N-isopropylamine | C8H16ClN | 详情 | 详情 | |
| (V) | 11434 | 2-(2-Chlorophenyl)-4-piperidinobutanenitrile | C15H19ClN2 | 详情 | 详情 | |
| (VI) | 51928 | 4-[allyl(isopropyl)amino]-2-(2-chlorophenyl)-2-[2-(1-piperidinyl)ethyl]butanenitrile | C23H34ClN3 | 详情 | 详情 | |
| (VII) | 51929 | 4-[allyl(isopropyl)amino]-2-(2-chlorophenyl)-2-[2-(1-piperidinyl)ethyl]butanamide | C23H36ClN3O | 详情 | 详情 | |
| (VIII) | 11438 | 2-(2-Chlorophenyl)-4-(isopropylamino)-2-(2-piperidinoethyl)butanamide | C20H32ClN3O | 详情 | 详情 |