2-Methoxyethanol → 2,2-Diphenyl-4-(4-azabicyclo[2. 2. 1]hept-7-yl)butyronitrile

HRID 328324

反応式

HRID 328324 の反応式
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11]Br)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]12[NH:25][CH:22]([CH2:23][CH2:24]1)CC2.CO[CH2:28][CH2:29]O>>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11][CH:19]2[N:25]3[CH2:22][CH2:23][CH:24]2[CH2:28][CH2:29]3)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 3

HCID 80192-MethoxyethanolHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 1360937-Azabicyclo(2.2.1)heptane

生成物 1

HCID 867346362,2-Diphenyl-4-(4-azabicyclo[2. 2. 1]hept-7-yl)butyronitrile

実験手順

15 Parts of 2,2-diphenyl-4-bromobutyronitrile are condensed with 12.9 parts of 7-azabicyclo[2. 2. 1]heptane by reflux in 100 parts by volume of ethylene glycol monomethyl ether. The reaction mixture is cooled and extracted with dilute hydrochloric acid. The aqueous hydrochloric acid extract is made basic with sodium hydroxide solution and extracted with ether. The ether extracts are dried over anhydrous sodium sulfate. Filtration and removal of the ether by evaporation at reduced pressure provides 2,2-diphenyl-4-(4-azabicyclo[2. 2. 1]hept-7-yl)butyronitrile, melting at 79°-81° C. 4.9 Parts of this butyronitrile, 1.5 parts of sodium azide, 1.2 parts of ammonium chloride, and 0.023 parts of lithium chloride are placed in 50 parts by volume of dimethylformamide and heated at 125° C for 12 hours. The mixture is cooled and the solid is filtered from the dimethylformamide. The solid is washed with dimethylformamide and water. The dried solid is 5-[1,1-diphenyl-3-(7-azabicyclo[2. 2. 1]hept-7-yl)]propyl-1H-tetrazole, melting at 284°-286° C.

後処理

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with dilute hydrochloric acid
  3. extractionThe aqueous hydrochloric acid extract
  4. extractionextracted with ether
  5. dry with materialThe ether extracts are dried over anhydrous sodium sulfate
  6. filtrationFiltration and removal of the ether
  7. customby evaporation at reduced pressure

出典と根拠

ORDレコード
ord-3f0be2b665174d40beddb186a63cbfc8
出典データセット
uspto-grants-1977_04
特許番号
US04017491

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