N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea -Drug Synthesis Database

【结构式】

【分子编号】54995

【品名】N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea

【CA登记号】

【分子式】C₂₁H₂₇N₃O

【分子量】337.465

【元素组成】C 74.74% H 8.06% N 12.45% O 4.74%

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：(XVIII)

Acetamide (XVI) was obtained by the Ritter reaction of 1-benzyl-4-phenyl-piperidin-4-ol (XV) with acetonitrile. Acidic hydrolysis of amide (XVI) provided the aminopiperidine (XVII), which was converted into urea (XVIII) upon treatment with N,N-dimethylcarbamoyl chloride. Hydrogenolytic cleavage of the N-benzyl group of (XVIII) gave piperidine (XIX), which was finally alkylated with the mesylate (XIV) to furnish the title compound.

参考文献中间体

合成目标

【1】 Emonds-Alt, X.; Grossriether, I.; Gueule, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthélabo); Substd. heterocyclic cpds., preparation method therefor and pharmaceutical compsns. containing same. EP 1156049; FR 2729952; FR 2729953; FR 2729954; JP 1999507324; JP 2001131171; US 5641777; WO 9623787 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIV)	54992	2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate	C₂₀H₂₁F₂NO₅S	详情	详情
(XV)	29470	1-benzyl-4-phenyl-4-piperidinol	C₁₈H₂₁NO	详情	详情
(XVI)	54993	N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide	C₂₀H₂₄N₂O	详情	详情
(XVII)	54994	1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine	C₁₈H₂₂N₂	详情	详情
(XVIII)	54995	N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea	C₂₁H₂₇N₃O	详情	详情
(XIX)	54996	N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea	C₁₄H₂₁N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Acidic hydrolysis of 4-acetylamino-1-benzyl-4-phenylpiperidine (I) gives diamine (II). Subsequent acylation of (II) with dimethylcarbamoyl chloride affords urea (III). The N-benzyl protecting group is then removed by catalytic hydrogenolysis over Pd/C to furnish piperidine (IV)

参考文献中间体

合成目标

【1】 Proietto, V.; Van Broeck, D.; Edmonds-Alt, X.; Aulombard, A. (Sanofi-Synthelabo); Ureidopiperidine derivs. as selective human NK3 receptor antagonists. EP 1119552; JP 2002527423; US 6465489; WO 0021931 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	54993	N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide	C₂₀H₂₄N₂O	详情	详情
(II)	54994	1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine	C₁₈H₂₂N₂	详情	详情
(III)	54995	N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea	C₂₁H₂₇N₃O	详情	详情
(IV)	54996	N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea	C₁₄H₂₁N₃O	详情	详情

Extended Information