4-Chloropyridine → 4-(Diallylamino)pyridine
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]>>[CH2:8]([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]Participants
Conditions
- Temperature
- 130 °C
Procedure
The title compound was prepared by hydrosilation of 4-diallylaminopyridine with dimethyl(ethoxy)silane, (EtO)Me2SiH. The 4-diallylaminopyridine was obtained by reaction of 4-chloropyridine with diallylamine. Thus, in an experiment similar to that described in Example 1, 4-chloropyridine (11.2 g; 0.10 mol) and diallylamine (14.6 g; 0.15 mol) were combined in an ampoule, degassed under vacuum, sealed and heated for three days at 130° C. The product mixture was dissolved in water, neutralized with 10% NaOH and extracted with several portions of diethyl ether. The ether solution was filtered, the solvent was evaporated, and the residue was distilled to give 4-diallylaminopyridine (11.3 g; 65%; b.p. 92° C. @ 0.25 torr). 4-Diallylaminopyridine (5.2 g; 0.030 mol), (EtO)Me2SiH (8.3 g; 0.080 mol), and H2PtCl6 (60 μL; 0.080 mol/L in isopropylalcohol (i--PrOH); 4.6×10 mol) were combined as in Example 1 and heated for 10 hours at 130° C. After reaction the product mixture was distilled under vacuum to give Silane 2a, N,N[bis(3-(dimethyl(ethoxy)silyl)propyl)-4-aminopyridine, as a colorless liquid (5.75 g; 50%; b.p. 142-146° C. @ 0.05 torr), which was also characterized by elemental analysis, infrared, 1H and 13C--NMR spectroscopy, and gas chromatography-mass spectrometry.
Workup
- customdegassed under vacuum
- customsealed
- dissolutionThe product mixture was dissolved in water
- extractionextracted with several portions of diethyl ether
- filtrationThe ether solution was filtered
- customthe solvent was evaporated
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-5d1873bb973143ef935d2cabbca1c202
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05442106
Reaction notes
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