Phosphine, diethyl- → Ethanamine, 2-(diethylphosphino)-N-[2-(diethylphosphino)ethyl]-

To a stirred solution of diethylphosphine (6.72 g, 74,6 mmol) in THF (150 ml) at −35° C., was added 47 ml of n-BuLi (1.6 M). Next, bis(2-chloroethyl)trimethylsilylamine (8.18 g, 38.4 mmol) in 40 ml tetrahydrofuran was then added dropwise to the LiP(Et)2 in tetrahydrofuran at −50° C. The mixture was allowed to warm to room temperature and stirred for 30 minutes. It was then heated to 60° C. and stirred overnight after which 100 ml of water was added to hydrolyse the silyl groups and the reaction mixture heated to 60° C. for 1 hour to ensure complete removal of the silyl groups. The reaction mixture was dried by passing it through a small bed of MgSO4, which was subsequently washed through with 60 ml diethyl ether. The solvent was removed to give 6.96 g bis(2-diethylphosphino-ethyl)-amine (Yield: 73%). 1H-NMR (C6D6) δ 1.12 (12H, d of t, CH2CH3, J=7.2 and 14.1 Hz), 1.38 (8H, q, CH2CH3, J=7.2), 1.60 (4H, t, (CH2)P, J=7.2) and 2.84 (4H, q, (CH2)N, J=7.8). 31P-NMR (C6D6) δ −26.02.

1. temperatureIt was then heated to 60° C.
2. additionwas added
3. temperaturethe reaction mixture heated to 60° C. for 1 hour
4. customremoval of the silyl groups
5. customThe reaction mixture was dried
6. washwas subsequently washed through with 60 ml diethyl ether
7. customThe solvent was removed

ORD record

ord-ffba5b100e734e90bfd9234306b02677

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361623B2