N-(1-benzyl-4-piperidinyl)urea -Drug Synthesis Database

【结构式】

【分子编号】34810

【品名】N-(1-benzyl-4-piperidinyl)urea

【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)

Condensation of 4-amino-1-benzylpiperidine (I) with benzoyl isocyanate gave the benzoyl urea (II), which was subsequently hydrolyzed to urea (III) with NaOH in aqueous methanol. Then, condensation of (III) with 2-hydroxypropiophenone (IV) in the presence of trifluoroacetic acid afforded a mixture of minor amounts of the required imidazolone (V) along with the major undesired regioisomer (VI).

参考文献中间体

合成目标

【1】 Carling, R.W.; Moyes, C.R.; Moore, K.W.; et al.; 1-(3-Cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1, 3-dihydroimidazol-2-one: A selective high-affinity antagonist for the human dopamine D(4) receptor with excellent selectivity over ion channels. J Med Chem 1999, 42, 14, 2706.
【2】 Carling, W.R.; Moore, K.W. (Merck Sharp & Dohme Ltd.); Imidazolone and oxazolone derivs. as dopamine antagonists. EP 0719264; JP 1997504272; US 5698573; WO 9507904 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	40601	benzoyl isocyanate	4461-33-0	C₈H₅NO₂	详情	详情
(I)	34808	1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine	50541-93-0	C₁₂H₁₈N₂	详情	详情
(II)	34809	N-benzoyl-N'-(1-benzyl-4-piperidinyl)urea		C₂₀H₂₃N₃O₂	详情	详情
(III)	34810	N-(1-benzyl-4-piperidinyl)urea		C₁₃H₁₉N₃O	详情	详情
(IV)	34811	2-hydroxy-1-phenyl-1-propanone		C₉H₁₀O₂	详情	详情
(V)	34812	1-(1-benzyl-4-piperidinyl)-5-methyl-4-phenyl-1,3-dihydro-2H-imidazol-2-one		C₂₂H₂₅N₃O	详情	详情
(VI)	34813	1-(1-benzyl-4-piperidinyl)-4-methyl-5-phenyl-1,3-dihydro-2H-imidazol-2-one		C₂₂H₂₅N₃O	详情	详情

Extended Information