N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea -Drug Synthesis Database

【结构式】

【分子编号】54996

【品名】N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)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 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(XIX)

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：(IV)

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

合成路线3

该中间体在本合成路线中的序号：(IV)

The previously reported (hydroxypropyl)piperidine derivative (V) is subjected to Swern oxidation to produce aldehyde (VI). Then, reductive amination of (VI) with piperidine (IV) in the presence of NaBH3CN affords the target compound

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
(IV)	54996	N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea	C₁₄H₂₁N₃O	详情	详情
(V)	29467	[(3S)-3-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)piperidinyl](phenyl)methanone	C₂₁H₂₃Cl₂NO₂	详情	详情
(VI)	60037	3-[(3S)-1-benzoyl-3-(3,4-dichlorophenyl)piperidinyl]propanal	C₂₁H₂₁Cl₂NO₂	详情	详情

Extended Information