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

HRID 849681Notes

Reaction equation

HRID 849681 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-029593bae0814334ad91f9c08f7cda4e
Source dataset
uspto-grants-2000_01
Patent number
US06013819

Reaction notes

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