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【结 构 式】

【分子编号】26920

【品名】3-(1-methyl-4-piperidinyl)-1H-indol-5-amine

【CA登记号】

【 分 子 式 】C14H19N3

【 分 子 量 】229.32508

【元素组成】C 73.33% H 8.35% N 18.32%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Condensation of 5-nitroindole (I) with 1-methyl-4-piperidone (II) in the presence of KOH produced tetrahydropyridinyl indole (III). Subsequent catalytic hydrogenation of (III) over Pd/C gave the 5-amino-3-piperidinylindole (VI). In a related procedure, 5-aminoindole (IV) was condensed with piperidone (II), and the resulting tetrahydropyridine (V) was hydrogenated to yield (VI). Aminoindole (VI) was finally condensed with 4-fluorobenzoyl chloride (VII) to produce the corresponding amide, which was isolated as the fumarate salt.

1 Audia, J.E.; Dressman, B.A.; Droste, J.J.; Fritz, J.E.; Kaldor, S.W.; Koch, D.J.; Krushinski, J.H. Jr.; Nissen, J.S.; Rocco, V.P.; Schaus, J.M.; Thompson, D.C. (Eli Lilly and Company); 5-Substd.-3-(1,2,3,6-tetrahydropyridin-4-yl)- and 3-(piperidin-4-yl)-1H-indoles: New 5-HT1F agonists. EP 0733628; JP 1999502816; US 5708008; WO 9629075 .
2 Johnson, K.W.; Phebus, L.A. (Eli Lilly and Company); Use of a serotonin 5-HT1F agonist in the manufacture of a medicament for treating or ameliorating the symptoms of common cold or allergic rhinitis. EP 0824917; US 5962473; WO 9806402 .
3 Johnson, K.W.; Phebus, L.A. (Eli Lilly and Company); A method for the prevention of migraine. WO 9811895 .
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) 26916 5-Nitroindole; 5-nitro-1H-indole 6146-52-7 C8H6N2O2 详情 详情
(II) 10919 1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one 1445-73-4 C6H11NO 详情 详情
(III) 26917 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole C14H15N3O2 详情 详情
(IV) 26918 Indole-5-amine; 1H-indol-5-ylamine; 5-Aminoindole 5192-03-0 C8H8N2 详情 详情
(V) 26919 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indol-5-amine C14H17N3 详情 详情
(VI) 26920 3-(1-methyl-4-piperidinyl)-1H-indol-5-amine C14H19N3 详情 详情
(VII) 17263 4-fluorobenzoyl chloride 403-43-0 C7H4ClFO 详情 详情
Extended Information