Tert-Butylamine → N-(tert-Butyl)-N-(cyclopentadienyldimethylsilyl)amine

HRID 1816470Notes

Reaction equation

HRID 1816470 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[Si:7]([CH:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([CH3:9])[CH3:8].C1CC=CC=1>C1COCC1>[C:1]([NH:5][Si:7]([CH:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 7612CyclopentadieneHCID 518808Cyclopentadienyl dimethyl chlorosilane

Product 1

HCID 12092871N-(tert-Butyl)-N-(cyclopentadienyldimethylsilyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.69 g (50.4 mmol) tert-butyl amine in 45 mL THF was added 2.00 g (12.6 mmol) (chloro)(cyclopentadienyl)(dimethyl)silane. Precipitate formed quickly. The slurry was stirred for several days, then the amine hydrochloride was filtered off and the solvent was removed under reduced pressure to give the product as a very pale yellowish oil. The yield was 2.069 g (84.2%). Mass spec: m/e 195 (6%). 1H and 13C NMR show the presence of several cyclopentadiene isomers.

Workup

  1. customPrecipitate formed quickly
  2. filtrationthe amine hydrochloride was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customto give the product as a very pale yellowish oil

Sources & evidence

ORD record
ord-3a5c25c1c3f8423da83bd6488f2bdbce
Source dataset
uspto-grants-2005_04
Patent number
US06884857B1

Reaction notes

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