N-[3-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】60994

【品名】N-[3-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]acetamide

【CA登记号】

【分子式】C₁₃H₁₆N₂O

【分子量】216.28292

【元素组成】C 72.19% H 7.46% N 12.95% O 7.4%

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：(XI)

N-Boc-4-Piperidone (VII) is converted into the enol triflate (VIII) upon treatment with N-phenyl trifluoromethanesulfonimide and LDA. Subsequent Suzuki coupling of (VIII) with 3-acetamidophenylboronic acid (IX) yields the 4-aryl tetrahydropyridine (X). Removal of the N-Boc group of (X) under acidic conditions furnishes the deprotected tetrahydropyridine (XI). Optionally, catalytic hydrogenation of (X) gives rise to piperidine (XII), which is then deprotected by acidic treatment to produce (XIII).

参考文献中间体

合成目标

【1】 Gluchowski, C.; Chiu, G.; Marzabadi, M.R.; Nagarathnam, D.; Lagu, B.; Noble, S.; Wetzel, J.; Deleon, J.E. (Synaptic Pharmaceutical Corp.); Selective melanin concentrating hormone-1 (MCH1) receptor antagonists and uses thereof. EP 1299362; WO 0206245 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	18620	tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone	79099-07-3	C₁₀H₁₇NO₃	详情	详情
(VIII)	32972	tert-butyl 4-[[(trifluoromethyl)sulfonyl]oxy]-3,6-dihydro-1(2H)-pyridinecarboxylate		C₁₁H₁₆F₃NO₅S	详情	详情
(IX)	60992	3-(acetylamino)phenylboronic acid		C₈H₁₀BNO₃	详情	详情
(X)	60993	tert-butyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate		C₁₈H₂₄N₂O₃	详情	详情
(XI)	60994	N-[3-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]acetamide		C₁₃H₁₆N₂O	详情	详情
(XII)	60995	tert-butyl 4-[3-(acetylamino)phenyl]-1-piperidinecarboxylate		C₁₈H₂₆N₂O₃	详情	详情
(XIII)	60996	N-[3-(4-piperidinyl)phenyl]acetamide		C₁₃H₁₈N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

Condensation of piperidine (XIII) with the N-bromopropyl derivative (VI) gives rise to the title compound. Alternatively, the title compound can be prepared by condensation of bromide (VI) with tetrahydropyridine (XI) to produce adduct (XIV), which is then hydrogenated over Pd/C.

参考文献中间体

合成目标

【1】 Gluchowski, C.; Chiu, G.; Marzabadi, M.R.; Nagarathnam, D.; Lagu, B.; Noble, S.; Wetzel, J.; Deleon, J.E. (Synaptic Pharmaceutical Corp.); Selective melanin concentrating hormone-1 (MCH1) receptor antagonists and uses thereof. EP 1299362; WO 0206245 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	60991	methyl (4S)-3-{[(3-bromopropyl)amino]carbonyl}-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate	C₁₈H₂₀BrF₂N₃O₅	详情	详情
(XI)	60994	N-[3-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]acetamide	C₁₃H₁₆N₂O	详情	详情
(XIII)	60996	N-[3-(4-piperidinyl)phenyl]acetamide	C₁₃H₁₈N₂O	详情	详情
(XIV)	60997	[1-(cyclopropylmethyl)-2-pyrrolidinyl]methanamine; [1-(cyclopropylmethyl)-2-pyrrolidinyl]methylamine	C₃₁H₃₅F₂N₅O₆	详情	详情

Extended Information