Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 1360602Notes

Reaction equation

HRID 1360602 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12]>[OH-].[Na+].CCOCC>[CH2:1]([NH:8][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamineYield 74.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
200 °C

Procedure

Benzylamine (51.5 g, 480 mmol) was added to (chloromethyl)trimethylsilane (19.64 g, 160 mmol) and heated at 200° C. for 2 hours. The reaction mixture was diluted with 1 N sodium hydroxide solution and ether and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was distilled under reduced pressure to afford 23.00 g of N-benzyl-N-trimethylsilanylmethyl-amine.

Workup

  1. dry with materialthe organic layer was dried over magnesium sulfate
  2. concentrationconcentrated under reduced pressure
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-4363f134f4304d89a1f0d3ef8dcdd64c
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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