Dimethyl Sulfoxide → HCID 21448660, compound

HRID 596824Notes

Reaction equation

HRID 596824 reaction equation
[C:1]([C:3]1([CH2:19][CH2:20]Br)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2)#[N:2].[ClH:22].[CH:23]12[CH2:30][CH2:29][CH:26]([CH2:27][CH2:28]1)[CH2:25][NH:24]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)C.C(Cl)Cl.C(O)(C)C.O>[ClH:22].[C:1]([C:3]1([CH2:19][CH2:20][N:24]2[CH2:25][CH:26]3[CH2:29][CH2:30][CH:23]2[CH2:28][CH2:27]3)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2)#[N:2]

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 2144866212-Cyano-12-(2-bromoethyl)-5,6,7,12-tetrahydrodibenzo[a,d]cycloocteneHCID 219848442-Azabicyclo[2.2.2]octane hydrochloride

Product 1

HCID 21448660HCID 21448660, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

3.1 Parts 12-cyano-12-(2-bromoethyl)-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene, 1.8 parts 2-azabicyclo[2.2.2]octane hydrochloride, 1.8 parts potassium carbonate, 44 parts dimethylsulfoxide and 10 parts water are combined, heated at 100° C. for about 4 hours, and then poured into an ice-water mixture. The resulting gummy precipitate is dissolved in a mixture of ethyl ether and methylene chloride. The organic phase is separated, washed three times with water, dried with sodium sulfate, filtered, and the solvents removed to leave an oil. This oil is dissolved with a solution of HC1 in isopropanol, and precipitated with ethyl ether to give 12-cyano12-[2-(2-azabicyclo[2.2.2]oct-2-yl)ethyl]-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene hydrochloride. This compound is represented by the following structural formula. ##STR17##

Workup

  1. customThe organic phase is separated
  2. washwashed three times with water
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvents removed
  6. customto leave an oil
  7. customprecipitated with ethyl ether

Sources & evidence

ORD record
ord-daee9cc1d34847c199d396dac081de17
Source dataset
uspto-grants-1977_03
Patent number
US04012393

Reaction notes

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