【结 构 式】 |
【分子编号】64584 【品名】8-[4-(4-fluorophenyl)-4-oxobutyl]-1,3,8-triazaspiro[4.5]decan-4-one 【CA登记号】 |
【 分 子 式 】C17H22FN3O2 【 分 子 量 】319.3791032 【元素组成】C 63.93% H 6.94% F 5.95% N 13.16% O 10.02% |
合成路线1
该中间体在本合成路线中的序号:(VIII)Similarly, the condensation of N-benzyl-4-piperidone (I) with KCN in the presence of NH4Cl provides amino nitrile (II), which is further hydrolyzed to amide (III) with 95% H2SO4. Cyclization of amino amide (III) with formamide under acidic conditions yields the spiro imidazolinone (IV), which is further reduced to imidazolidinone (V) employing NaBH4 in hot MeOH. Debenzylation of (V) with H2 and Pd/C provides 1,3,8-triazaspiro[4,5]decan-4-one (VI). Then, alkylation of (VI) with 4'-fluoro-4-chlorobutyrophenone (VII) by means of K2CO3 and catalytic KI in methyl isobutyl ketone furnishes (VIII). The imidazolidinone ring of (VIII) is finally methylated with iodomethane and KOH to produce the title compound (2).
【1】 Metwally, K.A.; Dukat, M.; Egan, C.T.; Smith, C.; Dupre, A.; Gauthier, C.B.; Herrick-Davis, K.; Teitler, M.; Glennon, R.A.; Spiperone: Influence of spiro ring substituents on 5-HT2A serotonin receptor binding. J Med Chem 1998, 41, 25, 5084. |
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) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
(II) | 64579 | 4-amino-1-benzyl-4-piperidinecarbonitrile | C13H17N3 | 详情 | 详情 | |
(III) | 64580 | 4-amino-1-benzyl-4-piperidinecarboxamide | C13H19N3O | 详情 | 详情 | |
(IV) | 64581 | 8-benzyl-1,3,8-triazaspiro[4.5]dec-2-en-4-one | C14H17N3O | 详情 | 详情 | |
(V) | 64582 | 8-benzyl-1,3,8-triazaspiro[4.5]decan-4-one | C14H19N3O | 详情 | 详情 | |
(VI) | 64583 | 1,3,8-triazaspiro[4.5]decan-4-one | C7H13N3O | 详情 | 详情 | |
(VII) | 35864 | 4-chloro-1-(4-fluorophenyl)-1-butanone | 3874-54-2 | C10H10ClFO | 详情 | 详情 |
(VIII) | 64584 | 8-[4-(4-fluorophenyl)-4-oxobutyl]-1,3,8-triazaspiro[4.5]decan-4-one | C17H22FN3O2 | 详情 | 详情 |