Methylamine → 1,5-Dimethyl-1-aza-4,6-dioxa-5-silacyclooctane

To a sealed 800 mL nitrogen purged glass bottle was added 400 mL anhydrous dichloromethane and 98.2 mL triethylamine. Then, 3.65 mL (35 mmol) of 99+% dichloromethylsilane and 4.02 mL (35 mmol) di(hydroxyethyl)methylamine was added with shaking. This was repeated five times over twenty minutes until a total of 175 mmol of both dichloromethylsilane and di(hydroxyethyl)methylamine had been added. The bottle was agitated in a room temperature bath for 15 minutes. Then, five more additions of 4.02 mL (35 mmol) 99+% dichloromethylsilane and 4.02 mL (35 mmol) dihydroxyethyl)methylamine were done until a total of 36.44 mL (0.35 mol) of 99+% dichloromethylsilane and 40.2 mL (0.35 mol) dihydroxyethylmethylamine were reached. The bottle was then agitated overnight in a room temperature bath. The resulting solution was filtered and dichloromethane removed by rotary evaporation. To the residue was added 400 mL of pentane and solution was filtered again. Pentane was removed by rotary evaporation and product was isolated by vacuum distillation at 78-81° C. and 20 mm Hg (41.7 g, 73.5% yield). 1H NMR (300 MHz, CDCl3) δ (ppm) 4.79 (1H, q), 3.83-3.71 (4H, m), 2.78-2.61 (4H, m), 2.37 (3H, s), 0.03 (3H, d).

1. customover twenty minutes
2. additionhad been added
3. stirringThe bottle was agitated in a room temperature bath for 15 minutes
4. stirringThe bottle was then agitated overnight in a room temperature bath
5. filtrationThe resulting solution was filtered
6. customdichloromethane removed by rotary evaporation
7. additionTo the residue was added 400 mL of pentane and solution
8. filtrationwas filtered again
9. customPentane was removed by rotary evaporation
10. customproduct was isolated by vacuum distillation at 78-81° C.

ORD record

ord-2fa6628cc409426e9895e86407d4443d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962745B2