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Water → HCID 20356962, compound

HRID 2083666
Notes
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Reaction equation

HRID 2083666 reaction equation
[CH2:1]1[CH:6]2[CH2:7][NH:8][CH:3]([CH2:4][CH2:5]2)[CH2:2]1.[ClH:9].O.[OH-].[K+].[C:13]1([C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH2:22][CH2:23]Br)[C:20]#[N:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[ClH:9].[C:25]1([C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([CH2:22][CH2:23][N:8]2[CH2:7][CH:6]3[CH2:5][CH2:4][CH:3]2[CH2:2][CH2:1]3)[C:20]#[N:21])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 219848442-Azabicyclo[2.2.2]octane hydrochloride

Product 1

HCID 20356962HCID 20356962, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent

Procedure

To a stirred solution of 0.85 part of 2-azabicyclo-[2.2.2.]octane hydrochloride in 20 parts of water is added 0.71 part of potassium hydroxide under a nitrogen atmosphere. Then, 1.90 parts of 2,2-diphenyl-4-bromobutyronitrile is added, and the mixture heated to reflux for 3.5 hours. This reaction mixture is cooled to about 60° C., whereupon 13 parts of benzene is added. The aqueous layer is separated and extracted with 15 parts of benzene. To the combined benzene extracts is added dropwise 2 parts by volume of a solution of hydrochloric acid in isopropanol. The volume of this solution is reduced by heating on a steam bath. Cooling affords a white precipitate which is washed with benzene and dried at 100° C. for about 2 hours. The resulting product, 2,2-diphenyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile hydrochloride, is obtained in approximately 76.8% yield. This product melts at about 194° - 197° C., and is represented by the following structural formula. ##STR11##

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3.5 hours
  3. additionis added
  4. customThe aqueous layer is separated
  5. extractionextracted with 15 parts of benzene
  6. additionTo the combined benzene extracts is added dropwise 2 parts by volume of a solution of hydrochloric acid in isopropanol
  7. temperatureby heating on a steam bath
  8. temperatureCooling
  9. customaffords a white precipitate which
  10. washis washed with benzene
  11. customdried at 100° C. for about 2 hours

Sources & evidence

ORD record
ord-ea72855d2b16432097a1b573c9cb1204
Source dataset
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04086234

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes