Acetic Acid → HCID 23313733, compound

HRID 745541Notes

Reaction equation

HRID 745541 reaction equation
Cl.[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]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1.C(O)(=O)C.[H][H]>[Pd].O>[ClH:2].[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]([CH2:18][CH2:17]3)[CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 70470812HCID 70470812, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23313733HCID 23313733, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Combine 2.0 g (7 mmole) of 3-[2-(4-chlorophenyl)ethylidene]-1-azabicyclo[2.2.2]octane hydrochloride, 40 ml of acetic acid, 0.2 g of 10% Pd/C catalyst and 5 ml of water. Place the mixture in a Parr apparatus and hydrogenate the mixture at ca. 43 p.s.i. Follow the reaction by the uptake of hydrogen. When the theoretical amount of hydrogen has been absorbed stop the reaction. Remove the catalyst by filtration and wash the catalyst with 40 ml of acetic acid. Remove the solvent from the filtrate in vacuo. Recrystallize the residue from 2-propanol to afford the title compound.

Workup

  1. customWhen the theoretical amount of hydrogen has been absorbed
  2. customthe reaction
  3. customRemove the catalyst
  4. filtrationby filtration
  5. washwash the catalyst with 40 ml of acetic acid
  6. customRemove the solvent from the filtrate in vacuo
  7. customRecrystallize the residue from 2-propanol

Sources & evidence

ORD record
ord-d4522c58568c49518f73d143db139f9a
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

Loading…