Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 2257417Notes

Reaction equation

HRID 2257417 reaction equation
Cl[CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:7]([NH:14][CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamine

Conditions

Temperature
120 °C

Procedure

A mixture of chloromethyltrimethylsilane (325 g, 370 ml, 2.65 mole) and benzylamine (835 g, 850 ml, 7.78 mole) was heated at 120°C. (oil bath temperature) for 2 h. A white solid began appearing after only 10 minutes and a viscous mixture eventually resulted. The reaction mixture was allowed to cool, then basified with potassium carbonate solution and extracted twice with ether. The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was purified by distillation. The excess benzylamine was removed in the first fractions (b.p. 47°-62°C. at 2 mmHg). The title compound (D11) was obtained as a colourless oil (380 g, 74%) b.p. 75°-80°C. at 2 mmHg.

Workup

  1. customa viscous mixture eventually resulted
  2. temperatureto cool
  3. extractionextracted twice with ether
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto leave a yellow oil, which
  7. distillationwas purified by distillation
  8. customThe excess benzylamine was removed in the first fractions (b.p. 47°-62°C. at 2 mmHg)

Sources & evidence

ORD record
ord-228af4b9686e4c2fb2d923f0471d1cd5
Source dataset
uspto-grants-1997_08
Patent number
USRE035593

Reaction notes

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