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【结 构 式】 
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【分子编号】41274 【品名】(1-butyl-4-piperidinyl)methanol 【CA登记号】 |
【 分 子 式 】C10H21NO 【 分 子 量 】171.28288 【元素组成】C 70.12% H 12.36% N 8.18% O 9.34% |
合成路线1
该中间体在本合成路线中的序号：(V)The chlorination of 8-acetamido-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (I) with chlorine in acetic acid gives the 7-chloro derivative (II), which is treated with aqueous NaOH to yield 8-amino-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (III). The reaction of (III) with carbonyldiimidazole (CDI) affords the activated intermediate (IV), which is finally condensed with 1-(1-butylpiperidin-4-yl)methanol (V) by means of MeLi in THF. The intermediate 1-(1-butylpiperidin-4-yl)methanol (V) has been obtained by condensation of piperidine-4-carboxylic acid ethyl ester (VI) with 1-bromobutane (VII) by means of K2CO3 in methanol, followed by reduction of the ester group with LiAlH4 in THF.
| 【1】 Bulteau, G.; Acher, J.; Thominet, M.; Collignon, C. (Ile de France); Substituted 2,3-alkylenedioxybenzamides. DE 2734270; FR 2360305; GB 1571278; GB 1571447; JP 53018570; US 4186135; US 4248885; US 4255580 . |
| 【2】 Gaster, L.M.; Sanger, G.J.; SB-204070: 5-HT4 receptor antagonists and their potential therapeutic utility. Drugs Fut 1994, 19, 12, 1109. |
| 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) | 41270 | 8-(acetamido)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid | C11H11NO5 | 详情 | 详情 | |
| (II) | 41271 | 8-(acetamido)-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid | C11H10ClNO5 | 详情 | 详情 | |
| (III) | 41272 | 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid | C9H8ClNO4 | 详情 | 详情 | |
| (IV) | 41273 | (8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)(1H-imidazol-1-yl)methanone | C12H10ClN3O3 | 详情 | 详情 | |
| (V) | 41274 | (1-butyl-4-piperidinyl)methanol | C10H21NO | 详情 | 详情 | |
| (VI) | 17410 | Ethyl isonipecotate; ethyl 4-piperidinecarboxylate | 1126-09-6 | C8H15NO2 | 详情 | 详情 |
| (VII) | 28721 | 1-bromobutane | 109-65-9 | C4H9Br | 详情 | 详情 |