HCID 20228803, compound → HCID 13728693, compound

HRID 1731303Notes

Reaction equation

HRID 1731303 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)/[CH:9]=[CH:10]/[N:11]([CH3:13])[CH3:12])[N:3]=1>C(O)C.[Pt]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:3]=1

Participants

4

Reactant 1

HCID 20228803HCID 20228803, compound

Product 1

HCID 13728693HCID 13728693, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of E-2-bromo-6-(1-(4-chlorophenyl)-3-dimethylaminoallyl)pyridine (vide supra (2.0 g) in absolute ethanol (150 mL) was stirred under hydrogen with 10% Pt/C (0.86 g) for 48 hr. The reaction mixture was filtered through Celite and the reduction continued with fresh catalyst (0.67 g) for an additional 96 hr. Filtration through Celite and concentration under reduced pressure gave an oil which was chromatographed on silica gel (Waters Prep 500) with 3:1/methanol:methylene chloride. This provided 2-bromo-6-(1-(4-chlorophenyl)-3-dimethylaminopropyl)pyridine (0.66 g) as an oil:TLC Rf 0.22 (silica gel, methanol).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. filtrationFiltration
  3. concentrationthrough Celite and concentration under reduced pressure
  4. customgave an oil which
  5. customwas chromatographed on silica gel (Waters Prep 500) with 3:1/methanol

Sources & evidence

ORD record
ord-414a6e2c3c164e8a825ae9c8ea8f47fd
Source dataset
uspto-grants-1986_11
Patent number
US04621094

Reaction notes

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