1-benzyl-4-(methylamino)-4-piperidinecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】64576

【品名】1-benzyl-4-(methylamino)-4-piperidinecarbonitrile

【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：(II)

The title compound is prepared by two related methods. N-Benzyl-4-piperidone (I) is condensed with KCN and MeNH2.HCl to produce amino nitrile (II). Partial hydrolysis of nitrile (II) with H2SO4 furnishes amide (III). Condensation of the amino amide (III) with triethyl orthoformate gives rise to the spiro imidazolinone (IV). Catalytic hydrogenation of the imidazoline double bond of (IV) and simultaneous N-benzyl group hydrogenolysis gives rise to 1-methyl-1,3,8-triazaspiro[4,5]decan-4-one (V). This is finally alkylated with 4'-fluoro-4-chlorobutyrophenone (VI) to yield the desired compound (1,2).

参考文献中间体

合成目标

【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.
【2】 Janssen, P.A.J. (Janssen Pharmaceutica NV); 2,4,8-Triaza-spiro(4,5)dec-2-enes. US 3155669 .

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)	64576	1-benzyl-4-(methylamino)-4-piperidinecarbonitrile		C₁₄H₁₉N₃	详情	详情
(III)	22019	1-benzyl-4-(methylamino)-4-piperidinecarboxamide	1024-11-9	C₁₄H₂₁N₃O	详情	详情
(IV)	64577	8-benzyl-1-methyl-1,3,8-triazaspiro[4.5]dec-2-en-4-one		C₁₅H₁₉N₃O	详情	详情
(V)	64578	1-methyl-1,3,8-triazaspiro[4.5]decan-4-one		C₈H₁₅N₃O	详情	详情
(VI)	35864	4-chloro-1-(4-fluorophenyl)-1-butanone	3874-54-2	C₁₀H₁₀ClFO	详情	详情

Extended Information