【结 构 式】 |
【分子编号】38641 【品名】1-(3-methyl-3-phenylbutyl)piperazine 【CA登记号】 |
【 分 子 式 】C15H24N2 【 分 子 量 】232.36904 【元素组成】C 77.53% H 10.41% N 12.06% |
合成路线1
该中间体在本合成路线中的序号:(IV)The cyclization of pyridine-3-carbaldehyde (I) with L-cysteine (II) gives 2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid (III), which is finally condensed with 1-(3-methyl-3-phenylbutyl)piperazine (IV) by means of DCC and HOBT In DMF. The intermediate 1-(3-methyl-3-phenylbutyl)piperazine (IV) has been obtained as follows: The reduction of 3-methyl-3-phenylbutyric acid (IV) with LiAlH4 in THF gives the corresponding butanol (V), which is treated with refluxing 48% HBr to yield the 3-methyl-3-phenylbutyl bromide (VI). The condensation of (VI) with piperazine-1-carboxylic acid ethyl ester (VII) by means of K2CO3 in 2-butanone gives 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylic acid ethyl ester (VIII), which is decarboxylated with NaOH in refluxing ethanol.
【1】 Mase, T.; Hara, H.; Nagaoka, H.; Takahasi, T.; Suzuki, T.; Tomioka, K.; Yamada, T. (Yamanouchi Pharmaceutical Co., Ltd.); Saturated heterocyclic carboxamide derivs.. AU 8812080; EP 0279681; JP 1988208582; US 4987132 . |
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) | 12849 | Nicotinaldehyde; 3-Pyridinecarboxaldehyde | 500-22-1 | C6H5NO | 详情 | 详情 |
(II) | 38633 | (2S)-2-amino-2-(methylsulfanyl)ethanoic acid | C3H7NO2S | 详情 | 详情 | |
(III) | 38634 | (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid | C9H10N2O2S | 详情 | 详情 | |
(IV) | 38637 | 3-methyl-3-phenylbutyric acid | C11H14O2 | 详情 | 详情 | |
(IV) | 38641 | 1-(3-methyl-3-phenylbutyl)piperazine | C15H24N2 | 详情 | 详情 | |
(V) | 38638 | 3-methyl-3-phenyl-1-butanol | C11H16O | 详情 | 详情 | |
(VI) | 38639 | 1-(3-bromo-1,1-dimethylpropyl)benzene | C11H15Br | 详情 | 详情 | |
(VII) | 24694 | N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine | 120-43-4 | C7H14N2O2 | 详情 | 详情 |
(VIII) | 38640 | ethyl 4-(3-methyl-3-phenylbutyl)-1-piperazinecarboxylate | C18H28N2O2 | 详情 | 详情 |