Acetic Acid → HCID 13971523, compound

HRID 745540Notes

Reaction equation

HRID 745540 reaction equation
[Br-:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=[C:11]2[CH:16]3[CH2:17][CH2:18][N+:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1.C(O)(=O)C>[Pd].O>[Br-:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[CH:16]3[CH2:15][CH2:14][N+:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:17]3)[CH2:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70471680HCID 70471680, compound

Product 1

HCID 13971523HCID 13971523, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Combine 2.47 g (0.08 mole) of 3-[2-(4-Chlorophenyl)ethylidene]-1-heptyl-1-azoniabicyclo[2.2.2]octane bromide, 50 ml of acetic acid, 0.26 g of 10% palladium on carbon and 5 ml of water in a Parr bottle and place the mixture on a Parr hydrogenation apparatus. Pressurize the system to 40 p.s.i. and follow the reaction by the pressure drop in the system. Filter the catalyst, remove the solvent in vacuo and triturate the residue with several portions of diethyl ether. Suspend the crude solid in 100 ml of water and adjust the mixture with 10% sodium hydroxide solution to pH 10. Extract the mixture with three 50 ml portions of ether. Adjust the mixture to pH 2 with hydrobromic acid and extract with four 75 ml portions of methylene chloride. Dry the combined organic extracts over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo. Recrystallize the residue from acetone to obtain the title compound.

Workup

  1. customthe reaction by the pressure drop in the system
  2. filtrationFilter the catalyst
  3. customremove the solvent in vacuo
  4. customtriturate the residue with several portions of diethyl ether
  5. extractionExtract the mixture with three 50 ml portions of ether
  6. extractionextract with four 75 ml portions of methylene chloride
  7. dry with materialDry the combined organic extracts over anhydrous sodium sulfate
  8. filtrationFilter the drying agent
  9. customremove the solvent in vacuo
  10. customRecrystallize the residue from acetone

Sources & evidence

ORD record
ord-782365f86eec4ea8b5ce99b63a30897a
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

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