Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 557927

Reaction equation

HRID 557927 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.[OH-].[Na+]>>[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 14798Sodium HydroxideHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamine

Conditions

Temperature
200 °C

Procedure

Into a round bottom 3-neck flask equipped with a nitrogen flow, a magnetic stirrer, and a fried richs condenser was added (chloromethyl)trimethylsilane (0.100 mol). To the flask was added benzylamine (0.300 mol), with stirring, and the resulting solution heated at 200° C. for 2.5 hours. Sodium hydroxide aqueous solution (0.1N) was added in order to hydrolyze the white organic salt that had formed. The mixture was extracted with ether and the ether layer was dried over magnesium sulfate and concentrated under reduced pressure through a Vigreux column to give the product at b.p. 68-72° C./0.7-0.8 mm.

Workup

  1. customInto a round bottom 3-neck flask equipped with a nitrogen flow, a magnetic stirrer, and a fried richs condenser
  2. customhad formed
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe ether layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure through a Vigreux column
  6. customto give the product at b.p. 68-72° C./0.7-0.8 mm

Sources & evidence

ORD record
ord-096651746a0848e689f9e72cc3bd31e8
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Linked notes

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