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【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

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).

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.

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
(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