4-amino-1-benzyl-4-piperidinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】64580

【品名】4-amino-1-benzyl-4-piperidinecarboxamide

【CA登记号】

【分子式】C₁₃H₁₉N₃O

【分子量】233.31348

【元素组成】C 66.92% H 8.21% N 18.01% O 6.86%

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：(III)

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).

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.

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

Extended Information