Phenyl(pyridin-3-yl)acetonitrile → 2-Phenyl-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile

HRID 1415151ノート

反応式

HRID 1415151 の反応式
[C:1]1([CH:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH:23]2[CH2:25][CH2:26][CH:20]1[CH2:21][CH2:22]2>C1(C)C=CC=CC=1>[C:1]1([C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)([CH2:17][CH2:18][N:19]2[CH2:24][CH:23]3[CH2:25][CH2:26][CH:20]2[CH2:21][CH2:22]3)[C:8]#[N:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 270956Phenyl(pyridin-3-yl)acetonitrileHCID 126123252-(2-Chloroethyl)-2-azabicyclo[2.2.2]octane

生成物 1

HCID 203569662-Phenyl-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

α-Phenyl-3-pyridylacetonitrile (U.S. Pat. No. 3,225,054) is reacted with 2-(2-chloroethyl)-2-azabicyclo[2.2.2]octane in toluene to provide 2-phenyl-2-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile. This nitrile is reacted with sodium azide in DMF containing lithium chloride to provide 5-[1-phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1H-tetrazole. Reaction this tetrazole with acetic anhydride in pyridine provides 5-[1-phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-2-methyl-1,3,4-oxadiazole, the oxalate salt melts at 171°-172° C.

出典と根拠

ORDレコード
ord-0d9de3fef5174e15a1c0482c643ed40e
出典データセット
uspto-grants-1977_01
特許番号
US04003904

反応ノート

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