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【结 构 式】 
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【分子编号】30408 【品名】(R)-(4-chlorophenyl)(phenyl)methylamine; (R)-(4-chlorophenyl)(phenyl)methanamine 【CA登记号】 |
【 分 子 式 】C13H12ClN 【 分 子 量 】217.69772 【元素组成】C 71.72% H 5.56% Cl 16.29% N 6.43% |
合成路线1
该中间体在本合成路线中的序号：(VI)In a further procedure, racemic (4-chlorophenyl)phenylmethyl amine (V) was resolved by means of L-tartaric acid. The undesired (S)-enantiomer (VII) could be recovered by racemization to (V) upon treatment with 2-hydroxybenzaldehyde and NaOMe. The required (R)-enantiomer (VI) was condensed with N,N-bis(chloroethyl)-p-toluenesulfonamide (VIII) in refluxing diisopropylethylamine to provide the N-tosyl piperazine (IX). Deprotection of the p-toluenesulfonamide of (IX) was achieved by treatment with HBr in the presence of 4-hydroxybenzoic acid. The resulting piperazine (X) was alkylated with either (2-chloroethoxy)acetamide (XI) or methyl (2-chloroethoxy)acetate (XIII), affording the N-alkylated piperazines (XII) and (XIV), respectively. The title carboxylic acid was then obtained by hydrolysis of amide (XII) with aqueous HCl or, alternatively, by hydrolysis of ester (XIV) with ethanolic KOH.
| 【1】 Bodson, G.; Gobert, J.; Cossement, E. (UCB SA); Enantiomers of 1-[4-(chlorophenyl)phenylmethyl]-4-(methylphenyl)sulfonyl piperazine. EP 0617028 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 30407 | p-Chloro benzhydryl amine; (4-Chlorophenyl)(phenyl)methylamine; (4-Chlorophenyl)(phenyl)methanamine | C13H12ClN | 详情 | 详情 | |
| (VI) | 30408 | (R)-(4-chlorophenyl)(phenyl)methylamine; (R)-(4-chlorophenyl)(phenyl)methanamine | C13H12ClN | 详情 | 详情 | |
| (VII) | 30413 | (S)-(4-chlorophenyl)(phenyl)methylamine; (S)-(4-chlorophenyl)(phenyl)methanamine | C13H12ClN | 详情 | 详情 | |
| (VIII) | 30409 | N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide | 42137-88-2 | C11H15Cl2NO2S | 详情 | 详情 |
| (IX) | 30410 | 1-[(R)-(4-chlorophenyl)(phenyl)methyl]-4-[(4-methylphenyl)sulfonyl]piperazine | C24H25ClN2O2S | 详情 | 详情 | |
| (X) | 30404 | 1-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazine | C17H19ClN2 | 详情 | 详情 | |
| (XI) | 16839 | 2-(2-chloroethoxy)acetamide | C4H8ClNO2 | 详情 | 详情 | |
| (XII) | 30411 | 2-(2-[4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl]ethoxy)acetamide | C21H26ClN3O2 | 详情 | 详情 | |
| (XIII) | 16841 | methyl 2-(2-chloroethoxy)acetate | C5H9ClO3 | 详情 | 详情 | |
| (XIV) | 30412 | methyl 2-(2-[4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl]ethoxy)acetate | C22H27ClN2O3 | 详情 | 详情 |