Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 1534883Notes

Reaction equation

HRID 1534883 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 (325g, 370ml, 2.65 mole) and benzylamine (835g, 850ml, 7.78 mole) was heated at 120° C. (oil bath temperature) for 2h. 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 2mmHg). The title compound (D16) was obtained as a colourless oil (380g, 74%) b.p. 75-80° C. at 2mmHg.

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 2mmHg)

Sources & evidence

ORD record
ord-077e080b697840ba9093e571ee597c66
Source dataset
uspto-grants-1992_02
Patent number
US05091397

Reaction notes

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