Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 2275640Notes

Reaction equation

HRID 2275640 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 friedrichs 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 friedrichs 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-6c28c3f4353a4ce4bc2ea3c22c9356e6
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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