Hydrochloric Acid → HCID 21448657, compound

HRID 596823Notes

Reaction equation

HRID 596823 reaction equation
[C:1]([C:3]1([CH2:18][CH2:19]Br)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].[ClH:21].[CH:22]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][NH:23]2.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)(C)C.C(OCC)C>[ClH:21].[C:1]([C:3]1([CH2:18][CH2:19][N:23]2[CH2:24][CH:25]3[CH2:28][CH2:29][CH:22]2[CH2:27][CH2:26]3)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19088473HCID 19088473, compoundHCID 219848442-Azabicyclo[2.2.2]octane hydrochloride

Product 1

HCID 21448657HCID 21448657, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 6.5 parts 5-cyano-5-(2-bromoethyl)10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 4.0 parts 2-azabicyclo[2.2.2]octane hydrochloride and 4.0 parts potassium carbonate in 88 parts N,N-dimethylsulfoxide and 20 parts water is heated at reflux for about 4 hours. After cooling, the reaction mixture is diluted with water, resulting in the formation of an oil. The water layer is decanted and the oil dissolved in ethyl ether. The ethereal solution is washed twice with water, once with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The solvent is removed to give an oil which is treated with a solution of hydrogen chloride in isopropanol. Addition of ethyl ether results in a precipitate that is separated, washed with ether and dried to afford-5-cyano-5[2-(2-azabicyclo[2.2.2]oct-2-yl)ethyl]-10,11-dihydro-5H-dibenzo[a,d]cycloheptene hydrochloride. This compound is represented by the following structural formula. ##STR14##

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 4 hours
  3. temperatureAfter cooling
  4. customresulting in the formation of an oil
  5. customThe water layer is decanted
  6. dissolutionthe oil dissolved in ethyl ether
  7. washThe ethereal solution is washed twice with water, once with a saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent is removed
  11. customto give an oil which
  12. customresults in a precipitate that
  13. customis separated
  14. washwashed with ether
  15. customdried

Sources & evidence

ORD record
ord-3fb9f6d6320d4adfbe98081382fc8a98
Source dataset
uspto-grants-1977_03
Patent number
US04012393

Reaction notes

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