Vinyltriethoxysilane → HCID 19070356, compound

HRID 1955498Notes

Reaction equation

HRID 1955498 reaction equation
[CH2:1]([C:8]([N:25]([CH3:27])[CH3:26])([CH2:23][CH3:24])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([Si:30]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH2:29]>C1(C)C=CC=CC=1>[CH2:1]([C:8]([N:25]([CH3:27])[CH3:26])([CH2:23][CH3:24])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:13][C:12]=1[CH2:29][CH2:28][Si:30]([O:31][CH2:32][CH3:33])([O:34][CH2:35][CH3:36])[O:37][CH2:38][CH3:39])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6516VinyltriethoxysilaneHCID 861712-Benzyl-2-(dimethylamino)-1-(4-(morpholin-4-yl)phenyl)butan-1-one

Product 1

HCID 19070356HCID 19070356, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.6 g (40 mmol) of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) -1-butanone, 750 mg (0.8 mmol) of RuH2 (CO) (PPh3)3 and 18.4 ml (88 mmol) of vinyltriethoxysilane were dissolved in 50 ml of toluene and degased using argon. After heating for 29 hours with stirring at reflux, the solvent was distilled off and the product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate). 22 g (100%) of a brown oil were obtained which were purified by boiling in heptane with active charcoal followed by filtration to give a yellow, viscous oil in a quantity of 20.6 g (95%). 1H-NMR (CDCl3): 0.64 ppm (3H, t, Bu-H4, 3JH,H =7.0 Hz); 1.10 ppm (2H, mc, Et-H2); 1.26 ppm (9H, t, CH3 of Si(OEt)3, 3JH,H =6.8 Hz); 1.88 ppm (2H, mc, Bu-H3); 2.36 ppm (6H, s, N(CH3)2); 2.72 ppm (2H, mc, Et-H1); 3.15 ppm (2H, mc, CH2 -Ph); 3.24 ppm (4H, mc, morpholine-N-CH2); 3.85 ppm (4H, mc, morpholine-o--CH2); 3.88 ppm (6H, q, SiOCH2); 6.60 ppm (1H, dd, Ph-H5, 3JH5,H6 =8.6 Hz, 4 JH3,H5 =2.6 Hz); 6.77 ppm (1H, d, Ph-H3); 7.12-7.28 ppm (5H, m, Ph'-H); 8.38 ppm (1H, d, Ph-H6).

Workup

  1. customdegased
  2. temperatureAfter heating for 29 hours
  3. temperatureat reflux
  4. distillationthe solvent was distilled off
  5. customthe product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate)

Sources & evidence

ORD record
ord-f96b84f7f7a441e98852c0482516d910
Source dataset
uspto-grants-1998_07
Patent number
US05776658

Reaction notes

Loading…