Vinyltrimethoxysilane → HCID 19070353, compound

HRID 1955497Notes

Reaction equation

HRID 1955497 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:35][CH3:36])([O:33][CH3:34])[O:31][CH3:32])=[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:35][CH3:36])([O:33][CH3:34])[O:31][CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76004VinyltrimethoxysilaneHCID 861712-Benzyl-2-(dimethylamino)-1-(4-(morpholin-4-yl)phenyl)butan-1-one

Product 1

HCID 19070353HCID 19070353, compoundYield 67%

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 13.4 ml (88 mmol) of vinyltrimethoxysilane were dissolved in 50 ml of toluene and degased using N2. After heating with stirring at reflux for 41 hours, the solvent was distilled off and the product was chromatographed (silica gel, CH2Cl2 /ethyl acetate). 13.8 g (67%) of dark red oil were obtained which were purified by boiling in heptane with active charcoal followed by filtration to give a yellow, viscous oil. 1H-NMR (CDCl3): 0.61 ppm (3H, t, Bu-H4, 3JH,H =7.2 Hz); 1.2 ppm (2H, mc, Et-H2); 1.88 ppm (2H, mc, Bu-H3); 2.37 ppm (6H, s, N(CH3)2); 2.71 ppm (2H, mc, Et-H1); 3.16 ppm (2H, mc, CH2 -Ph); 3.25 ppm (4H, mc, morpholine-N--CH2); 3.63 ppm (9H, s, Si(OCH3)3); 3.85 ppm (4H), mc, morpholine-O-CH2); 6.61 ppm (1H, dd, Ph-H5, 3JH5,H6, =8.6 Hz, 4 JH3, H6 =2.6 Hz); 6.75 ppm (1H, d, Ph-H3); 7.14-7.29 ppm (5H, m, Ph'-H); 8.44 ppm (1H, d, Ph-H6).

Workup

  1. customdegased
  2. temperatureAfter heating
  3. temperatureat reflux for 41 hours
  4. distillationthe solvent was distilled off
  5. customthe product was chromatographed (silica gel, CH2Cl2 /ethyl acetate)

Sources & evidence

ORD record
ord-db06e0d327474187bdbb0d431c2a3536
Source dataset
uspto-grants-1998_07
Patent number
US05776658

Reaction notes

Loading…