Benzene → 1-(2-Azabicyclo[2.2.2]octan-2-yl)-3,3,3-triphenylpropan-1-one

HRID 1973693

반응식

HRID 1973693 반응식
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:22][C:23](O)=[O:24].[CH:28]12[CH2:35][CH2:34][CH:31]([CH2:32][CH2:33]1)[CH2:30][NH:29]2.C1C=CC=CC=1>C(O)C>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:22][C:23]([N:29]2[CH2:30][CH:31]3[CH2:34][CH2:35][CH:28]2[CH2:33][CH2:32]3)=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 241BenzeneHCID 867Malonic AcidHCID 6457TriphenylcarbinolHCID 92362-Azabicyclo(2.2.2)octane

생성물 1

HCID 203569181-(2-Azabicyclo[2.2.2]octan-2-yl)-3,3,3-triphenylpropan-1-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2 parts of triphenyl carbinol and 8 parts of malonic acid are heated at 170° for 3 hours. This mixture is cooled and dissolved in hot ethanol. 3,3,3-Triphenylpropionic acid, melting at 182°, crystallizes from the ethanol upon cooling. 1 Part of 3,3,3-triphenylpropionic acid is refluxed with 5 parts of thionyl chloride for 4 hours and the excess thionyl chloride is removed in vacuum to provide the crude 3,3,3-triphenyl propionyl chloride. 1 Part of this acid chloride is reacted with 2 parts of 2-azabicyclo[2. 2. 2]octane in 50 parts of benzene. The precipitated amide is filtered and the benzene solution washed with water, dried with magnesium sulfate, and the benzene evaporated. The remaining oil is crystallized to provide 2-(3,3,3-triphenylpropionyl)-2-azabicyclo[2. 2. 2]octane. 0.9 Parts of this material is reacted with 0.37 parts of lithium aluminum hydride in 15 parts of tetrahydrofuran at reflux for 5 hours. The reaction mixture is cooled and treated with 15% aqueous sodium hydroxide solution to decompose any unreacted lithium aluminum hydride. The reaction mixture is filtered and the solvent is removed in vacuo to provide a residual oil which is taken up in ether. The ether soln. is extracted c 10% HCl forming an insoluble gum, which is dissolved in methylene chloride, dried over anhydrous sodium sulfate and evaporated providing 2-(3,3,3-triphenylpropyl)-2-azabicyclo[2. 2. 2]octane hydrochloride, melting at 222°-223° C. This compound has the following molecular formula. ##STR30##

후처리

  1. temperatureare heated at 170° for 3 hours
  2. temperatureThis mixture is cooled
  3. custom3,3,3-Triphenylpropionic acid, melting at 182°, crystallizes from the ethanol
  4. temperatureupon cooling
  5. temperature1 Part of 3,3,3-triphenylpropionic acid is refluxed with 5 parts of thionyl chloride for 4 hours
  6. customthe excess thionyl chloride is removed in vacuum
  7. customto provide the crude 3,3,3-triphenyl propionyl chloride
  8. filtrationThe precipitated amide is filtered
  9. washthe benzene solution washed with water
  10. dry with materialdried with magnesium sulfate
  11. customthe benzene evaporated
  12. customThe remaining oil is crystallized

출처 및 근거

ORD 기록
ord-769c985b76664e57b5a5078a041c527f
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03998832

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