Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 1766629Notes

Reaction equation

HRID 1766629 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(#N)C>[CH3:4][Si:3]([CH2:2][NH:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamineYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of chloromethyltrimethylsilane (1.34 kg, 10.96 mol) in acetonitrile (17.0 L) is added benzylamine (2.34 kg, 21.92 mol) and the reaction mixture is heated at reflux for 16 h. The reaction mixture is cooled to room temperature and the precipitate of benzylamine hydrochloride is removed by filtration. The filtrate is concentrated under vacuum to about 5 L and then diluted with water (5 L). The reaction mixture is extracted with hexane (2×5 L). The organic extracts are combined and washed with brine (5 L) and dried over MgSO4. The filtrate is concentrated under vacuum to give 1.77 kg (83%) of N-(trimethylsilylmethyl)benzylamine.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 16 h
  3. customthe precipitate of benzylamine hydrochloride is removed by filtration
  4. concentrationThe filtrate is concentrated under vacuum to about 5 L
  5. additiondiluted with water (5 L)
  6. extractionThe reaction mixture is extracted with hexane (2×5 L)
  7. washwashed with brine (5 L)
  8. dry with materialdried over MgSO4
  9. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-4c06a95212b7427288d50bbfcc06230b
Source dataset
uspto-grants-2007_06
Patent number
US07230119B2

Reaction notes

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