Water → N-[(Trimethylsilyl)methyl]benzylamine

To a stirred solution of chloromethyl-trimethyl-silane (25 g, 203.79 mmol, 1 eq.) in acetonitrile (250 mL) was added distilled benzyl amine (44.56 mL, 407.59 mmol, 2 eq) at room temperature. Resulting reaction mixture was refluxed for 16 hours. After consumption of starting material, reaction mixture was cooled to room temperature; benzyl amine hydrochloride salt was precipitate out. Solid was removed by filtration and filtrate was concentrated under reduced pressure to get yellow semi solid. Water was added to residue and extracted with ethyl acetate (3×100 mL). Combined organic layer was washed with brine (200 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford product as yellow liquid (25 g, crude). Crude used as such for next reaction. 1H-NMR (400 MHz, CDCl3) δ: 0.03 (s, 9H), 2.04 (s, 2H), 3.79 (s, 2H), 3.86 (s, 1H), 7.29-7.33 (m, 5H). (m/z): 193.8 (M+H)

1. customResulting
2. customreaction mixture
3. temperaturewas refluxed for 16 hours
4. customAfter consumption of starting material, reaction mixture
5. custombenzyl amine hydrochloride salt was precipitate out
6. customSolid was removed by filtration and filtrate
7. concentrationwas concentrated under reduced pressure
8. customto get yellow semi solid
9. extractionextracted with ethyl acetate (3×100 mL)
10. washCombined organic layer was washed with brine (200 mL)
11. dry with materialdried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure

ORD record

ord-583a113cabc44e12a3b80d051888f78a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221835B2