Hydrochloric Acid → 4-[4-Azatricyclo(4.3,1.13,8)undecan-4-yl]-2,2-diphenylbutanenitrile

HRID 2398645Notes

Reaction equation

HRID 2398645 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:19][CH2:20][N:21]1[CH2:29][CH:28]2[CH2:30][CH:24]3[CH2:25][CH:26]([CH2:31][CH:22]1[CH2:23]3)[CH2:27]2.Cl>O.C1(C)C=CC=CC=1>[CH:24]12[CH2:30][CH:28]3[CH2:27][CH:26]([CH2:31][CH:22]([N:21]([CH2:20][CH2:19][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:8]#[N:9])[CH2:29]3)[CH2:23]1)[CH2:25]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 539394214-(2-Chloroethyl)-4-azatricyclo[4.3.1.13,8]undecane

Product 1

HCID 538812994-[4-Azatricyclo(4.3,1.13,8)undecan-4-yl]-2,2-diphenylbutanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 18 parts of α-phenylbenzeneacetonitrile in 140 parts of dry toluene is added, with stirring under nitrogen, approximately 4 parts of a 57% dispersion of sodium hydride in oil. The resultant mixture is heated to 90° and stirred thereat under nitrogen for 3/4 hr. The yellow-green flocculent suspension which eventuates is cooled to around 65°, whereupon 20 parts of 4-(2-chloroethyl)-4-azatricyclo[4.3.1.13,8 ]undecane [preparable by mixing the hydrochloride thereof (U.S. Pat. No. 3,845,038) with excess aqueous sodium carbonate, extracting the mixture with toluene, and consecutively washing the extract with water, drying it over anhydrous sodium sulfate, filtering out the drying agent, and removing the solvent by vacuum distillation] in 85 parts of dry toluene is introduced, with stirring, during 15 minutes. The mixture thus obtained is stirred for 2 hours at 90°-100°. The yellow-orange solution which results is cooled to room temperature, at which point 20 parts of water is stirred in. Aqueous and organic phases are separated, the aqueous phase is extracted with toluene and then discarded, and the extract and organic phases are combined and thereupon consecutively washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate is stripped of solvent by vacuum distillation, affording 4-[4-azatricyclo(4.3,1.13,8)undecan-4-yl]-2,2-diphenylbutanenitrile as the residue. The product has the formula ##STR9##

Workup

  1. stirringstirred
  2. waitunder nitrogen for 3/4 hr
  3. extraction3,845,038) with excess aqueous sodium carbonate, extracting the mixture with toluene
  4. washconsecutively washing the
  5. extractionextract with water
  6. dry with materialdrying it over anhydrous sodium sulfate
  7. filtrationfiltering out the drying agent
  8. customremoving the solvent
  9. distillationby vacuum distillation] in 85 parts of dry toluene
  10. additionis introduced
  11. stirringwith stirring, during 15 minutes
  12. customThe mixture thus obtained
  13. stirringis stirred for 2 hours at 90°-100°
  14. customThe yellow-orange solution which results
  15. stirringis stirred in
  16. customAqueous and organic phases are separated
  17. extractionthe aqueous phase is extracted with toluene
  18. extractionthe extract
  19. washconsecutively washed with water
  20. dry with materialdried over anhydrous sodium sulfate
  21. filtrationfiltered
  22. distillationThe filtrate is stripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-8fb3648d4c9a4c388b36ad11d1d2e7ff
Source dataset
uspto-grants-1977_05
Patent number
US04025524

Reaction notes

Loading…