2-(1-Benzylpiperidin-4-yl)ethan-1-amine → 5-(Quinuclidin-3-yl)-3-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]-1,2,4-oxadiazole

反応式

C(O[C:4]([C:6]1[N:10]=[C:9]([CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)[O:8][N:7]=1)=[O:5])C.[CH2:19]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[N:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[CH:11]([C:9]1[O:8][N:7]=[C:6]([C:4](=[O:5])[NH:34][CH2:33][CH2:32][CH:29]3[CH2:28][CH2:27][N:26]([CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:31][CH2:30]3)[N:10]=1)[CH2:12]2

参加物

反応物 2

HCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amine

HCID 146855463-Ethoxycarbonyl-5-(quinuclidin-3-yl)-1,2,4-oxadiazole

生成物 1

HCID 199591655-(Quinuclidin-3-yl)-3-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]-1,2,4-oxadiazole

反応条件

温度: 100 °C

実験手順

A mixture of 3-ethoxycarbonyl-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.2 g) and 1-benzyl-4-(2-aminoethyl)piperidine (0.26 g) was stirred and heated at 100° C. for 2 hours. The cooled mixture was chromatographed on alumina eluting with chloroform to give 5-(quinuclidin-3-yl)-3-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]-1,2,4-oxadiazole as an oil. The compound was treated with an ethanol solution of hydrogen chloride, the solution was evaporated in vacuo and the residue was powdered with ether to give 5-(quinuclidin-3-yl)-3-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]-1,2,4-oxadiazole dihydrochloride (0.2 g).

後処理

customThe cooled mixture was chromatographed on alumina eluting with chloroform

出典と根拠

ORDレコード: ord-f63717e5f49849a488f00827e3ebbd54
出典データセット: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05622976

反応ノート

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