Hydrochloric Acid → 4-Azatricyclo[4.3.1.13,8]undecane

HRID 2083582Notes

Reaction equation

HRID 2083582 reaction equation
C1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[N:10]C=C[CH:13]=2)C=CC=CC=1.C([Li])CCC.ClCCN1CC2CC3CC(CC1C3)C2.Cl>C1CCCCC1>[CH:14]12[CH2:7][CH:8]3[CH2:13][CH:16]([CH2:17][CH:18]([NH:10][CH2:9]3)[CH2:19]1)[CH2:15]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 772513-BenzhydrylpyridineHCID 539394214-(2-Chloroethyl)-4-azatricyclo[4.3.1.13,8]undecaneHCID 178418339Butyllithium

Product 1

HCID 322724-Azatricyclo[4.3.1.13,8]undecane

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Reaction of 2.5 parts of diphenyl-3-pyridylmethane in 60 parts by volume of cyclohexane with an equivalent amount of butyl lithium at 10° C under nitrogen is followed by the addition of 2.1 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]. Quenching of the reaction with water and isolation by extraction with ether, washing, drying and evaporation of solvent provides 4-[3,3-(diphenyl)-3-(3-pyridyl)propyl[-4-azatricyclo[4.3.1.13,8 ]undecane having the following structural formula ##STR52##

Workup

  1. extraction3,845,038) with excess aqueous sodium carbonate, extracting the mixture with toluene
  2. washconsecutively washing the
  3. extractionextract with water
  4. dry with materialdrying it over anhydrous sodium sulfate
  5. filtrationfiltering out the drying agent
  6. customremoving the solvent
  7. distillationby vacuum distillation]
  8. customQuenching of the reaction with water and isolation by extraction with ether
  9. washwashing
  10. customdrying
  11. customevaporation of solvent

Sources & evidence

ORD record
ord-f1e7008cd2014a1f8404e94f2d073f00
Source dataset
uspto-grants-1978_04
Patent number
US04086227

Reaction notes

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