4-(2-methylphenyl)-4-piperidinecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】43941

【品名】4-(2-methylphenyl)-4-piperidinecarbonitrile

【CA登记号】

【分子式】C₁₃H₁₆N₂

【分子量】200.28352

【元素组成】C 77.96% H 8.05% N 13.99%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The intermediate piperidine (IV) was prepared by bis-alkylation of o-methylphenylacetonitrile (I) with N-Boc-bis(2-chloroethyl)amine (II), followed by deprotection of the resulting N-Boc-piperidine (III) with HCl in EtOAc.

参考文献中间体

合成目标

【1】 Newton, R.C.; Freidinger, R.M.; Price, R.A.; Chang, R.S.L.; Patane, M.A.; DiPardo, R.M.; Di Salvo, J.; Broten, T.P.; Ransom, R.W.; Bock, M.G.; Cyclic imides as potent and selective alpha-1A adrenergic receptor antagonists. Bioorg Med Chem Lett 2001, 11, 14, 1959.
【2】 Bell, M.G.; DiPardo, R.M.; Crowell, T.A.; et al.; Cyclic imides as potent and selective alpha-1A adrenergic receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 298.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	43938	2-(2-methylphenyl)acetonitrile	C₉H₉N	详情	详情
(II)	43939	tert-butyl bis(2-chloroethyl)carbamate	C₉H₁₇Cl₂NO₂	详情	详情
(III)	43940	tert-butyl 4-cyano-4-(2-methylphenyl)-1-piperidinecarboxylate	C₁₈H₂₄N₂O₂	详情	详情
(IV)	43941	4-(2-methylphenyl)-4-piperidinecarbonitrile	C₁₃H₁₆N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Di-tolylacetic acid (V) was converted into the benzyl ester (VI) using benzyl bromide and K2CO3 in DMF. Subsequent alpha-alkylation of ester (VI) with ethyl bromoacetate provided diester (VII). The benzyl ester group of (VII) was then removed by hydrogenolysis over Pd/C. Condensation of the resulting mono-acid (VIII) with 3-bromopropylamine (IX) in the presence of EDC and HOBt furnished the N-(bromopropyl)succinimide (X). This was finally condensed with piperidine (IV) to provide the title compound.

参考文献中间体

合成目标

【1】 Newton, R.C.; Freidinger, R.M.; Price, R.A.; Chang, R.S.L.; Patane, M.A.; DiPardo, R.M.; Di Salvo, J.; Broten, T.P.; Ransom, R.W.; Bock, M.G.; Cyclic imides as potent and selective alpha-1A adrenergic receptor antagonists. Bioorg Med Chem Lett 2001, 11, 14, 1959.
【2】 Bell, M.G.; DiPardo, R.M.; Crowell, T.A.; et al.; Cyclic imides as potent and selective alpha-1A adrenergic receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 298.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	43941	4-(2-methylphenyl)-4-piperidinecarbonitrile		C₁₃H₁₆N₂	详情	详情
(V)	43942	2,2-bis(4-methylphenyl)acetic acid		C₁₆H₁₆O₂	详情	详情
(VI)	43943	benzyl 2,2-bis(4-methylphenyl)acetate		C₂₃H₂₂O₂	详情	详情
(VII)	43944	1-benzyl 4-ethyl 2,2-bis(4-methylphenyl)succinate		C₂₇H₂₈O₄	详情	详情
(VIII)	43945	4-ethoxy-2,2-bis(4-methylphenyl)-4-oxobutyric acid		C₂₀H₂₂O₄	详情	详情
(IX)	25449	3-bromo-1-propanamine; 3-bromopropylamine	18370-81-5	C₃H₈BrN	详情	详情
(X)	43946	1-(3-bromopropyl)-3,3-bis(4-methylphenyl)-2,5-pyrrolidinedione		C₂₁H₂₂BrNO₂	详情	详情

Extended Information