N-phenyl-N'-[2-(4-piperidinyl)ethyl]urea -Drug Synthesis Database

【结构式】

【分子编号】25202

【品名】N-phenyl-N'-[2-(4-piperidinyl)ethyl]urea

【CA登记号】

【分子式】C₁₄H₂₁N₃O

【分子量】247.34036

【元素组成】C 67.98% H 8.56% N 16.99% O 6.47%

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：(IV)

Condensation of 2-(1-benzyl-4-piperidinyl)ethyl amine (I) with phenyl isocyanate (II) provided the corresponding urea (III), which was debenzylated by hydrogenolysis over Pd/C to afford the secondary amine (IV). Subsequent Mannich reaction of (IV) with 4-chromanone (V) and paraformaldehyde produced the (chromanylmethyl)piperidine (VI). After ketone reduction of (IV) by means of NaBH4, the resulting alcohol (VII) was dehydrated in refluxing 6 N HCl to furnish the target chromene.

参考文献中间体

合成目标

【1】 Mayer, P.; et al.; Modulation of the benzodioxane heterocycle in a novel series of potent alpha2 adrenoceptor antagonists. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 112.
【2】 Vidaluc, J.-L.; Imberg, T.; Marien, M.; Briley, M. (Pierre Fabre Medicament); Novel benzodioxanes and 1-(2H)-benzopyranes, their preparation and their use as medicine. WO 9802435 .

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)	17606	2-(1-benzyl-4-piperidinyl)-1-ethanamine; 2-(1-benzyl-4-piperidinyl)ethylamine		C₁₄H₂₂N₂	详情	详情
(II)	11289	1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate	103-71-9	C₇H₅NO	详情	详情
(III)	25201	N-[2-(1-benzyl-4-piperidinyl)ethyl]-N'-phenylurea		C₂₁H₂₇N₃O	详情	详情
(IV)	25202	N-phenyl-N'-[2-(4-piperidinyl)ethyl]urea		C₁₄H₂₁N₃O	详情	详情
(V)	14461	2,3-Dihydro-4H-chromen-4-one; 4-Chromanone	491-37-2	C₉H₈O₂	详情	详情
(VI)	25203	N-(2-[1-[(4-oxo-3,4-dihydro-2H-chromen-3-yl)methyl]-4-piperidinyl]ethyl)-N'-phenylurea		C₂₄H₂₉N₃O₃	详情	详情
(VII)	25204	N-(2-[1-[(4-hydroxy-3,4-dihydro-2H-chromen-3-yl)methyl]-4-piperidinyl]ethyl)-N'-phenylurea		C₂₄H₃₁N₃O₃	详情	详情

Extended Information