Chlorotrimethylsilane → HCID 15490765, compound

Temperature

10 °C

Under argon, in a 500 ml Schlenk flask containing a magnetic stir bar, 49.38 g (0.480 mol) of 3-dimethylaminopropylamine (99%, Aldrich) was added to 120 ml of anhydrous hexanes (distilled from Na). This mixture was stirred and cooled with a constant temperature bath at 10° C. From a dropping funnel, 25 g of TMS—Cl (0.230 mol) were added dropwise to the mixture over a period of two hours. A white precipitate formed, and later redissolved forming a separate layer at the bottom of the flask. Once the TMS—Cl addition was complete, 200 ml of anhydrous ether (distilled from Na/K) was added to the flask. The mixture then was rapidly stirred overnight causing the two layers to merge into a homogeneous solution over a white precipitate. The solution was separated from the white solid by cannulation and distilled at ambient pressure to give TMS—NH—CH2CH2CH2NMe2 at 160° C. Yield: 85%. Characterization: 1H NMR: (400 MHz, positive δ downfield referenced to Si(CH3)4=0 ppm utilizing residual CDCl3=7.24 ppm in solvent CDCl3) 2.72 [m, 2H, —CH2NMe2], 2.24 [(m, 2H, TMS—NH—CH2—], 2.20 [s, 6H, —NCH3], 1.54 [m, 4H, TMS—NH—CH2CH2—], 0.02 [s, 18H, CH3Si—]. 13C{1H} NMR: (75 MHz, positive δ downfield referenced to Si(CH3)4=0 ppm utilizing residual C6D5H=128.0 ppm in solvent C6D6) 57.45 [—CH2NMe2], 45.40 [—NCH3], 40.00 [TMS—N—CH2—], 32.66 [TMS—N—CH2CH2—], −0.20 [(CH3)3Si—N—]. Mass Spectrum: (EI, 70 eV) 174 [TMS—NHCH2CH2CH2NMe2]+, 159 (M—Me), 129, 114, 100, 85, 72, 58.

1. additionUnder argon, in a 500 ml Schlenk flask containing a magnetic stir bar
2. customA white precipitate formed
3. dissolutionlater redissolved
4. customforming a separate layer at the bottom of the flask
5. customThe solution was separated from the white solid by cannulation
6. distillationdistilled at ambient pressure

ORD record

ord-2a6c22789fcf47ec9f305df96094dc65

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265597B1