4-Chloropyridine → 4-(Diallylamino)pyridine

HRID 1034328Notes

Reaction equation

HRID 1034328 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([NH:11][CH2:12][CH:13]=[CH2:14])[CH:9]=[CH2:10].[CH2:15]([O:17][CH:18]([SiH3:22])[O:19][CH2:20][CH3:21])[CH3:16]>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH2:8]([N:11]([CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH:9]=[CH2:10].[CH2:15]([O:17][CH:18]([SiH2:22][CH2:10][CH2:9][CH2:8][N:11]([CH2:12][CH2:13][CH2:14][SiH2:22][CH:18]([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[O:19][CH2:20][CH3:21])[CH3:16]

Participants

6

Reactant 3

HCID 122884-ChloropyridineHCID 31279DiallylamineHCID 57375577Diethoxymethylsilane

Product 2

HCID 108776384-(Diallylamino)pyridineHCID 1317184144-Bis(3'-diethoxymethylsilylpropyl)aminopyridine

Reagents, catalysts & solvents 1

HCID 61859Chloroplatinic acidCatalyst

Procedure

4-Diallylaminopyridine was prepared by the condensation of 4-chloropyridine with diallylamine, as described by Mathias and Cei (Macromolecules, 1987, 20, 2645). This product was hydrosilylated with diethoxymethylsilane in the presence of chloroplatinic acid, as described by Rubinsztajn, et al, (Macromolecules, 1990, 23, 4026) to yield 4-bis(3'-diethoxymethylsilylpropyl)aminopyridine. Finally, following a procedure similar to that described by Tundo and Venturello (J. Amer. Chem. Soc., 1979, 101, 6606), this product was heated with activated silica (Davison Grade 22, 60-200 mesh, 60 Angstrom, 500 m2 /gram BET surface area, 0.75 cm3 /gram pore volume), to give the silica bound dialkylaminopyridine with the loss of ethanol. After drying in a vacuum oven at 45° C. for 18 hours, this material found to contain 0.6 meq aminopyridine/gram.

Sources & evidence

ORD record
ord-506f9d612ed34d9799cea27a8d360514
Source dataset
uspto-grants-1994_05
Patent number
US05315004

Reaction notes

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