Silane, (chloromethyl)trimethyl- → HCID 67244917, compound

HRID 2425525Notes

Reaction equation

HRID 2425525 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[CH3:11][Si:12]([CH2:15]Cl)([CH3:14])[CH3:13]>C(#N)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 75361Silane, (chloromethyl)trimethyl-HCID 812922-Methoxybenzylamine

Product 1

HCID 67244917HCID 67244917, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methoxybenzylamine (25 g, 182.2 mmol) and trimethylsilylmethyl chloride (11.2 g, 91.1 mmol) in acetonitrile (140 ml) was refluxed overnight. Then the mixture was concentrated under vacuum at 70° C. with a rotary evaporator to remove all volatiles. The white residue was mixed with n-heptane (250 ml) and filtered over a glass filter. The salt residue was washed with n-heptane (2×25 ml). The combined heptane filtrates were concentrated under vacuum to give the crude product 2-methoxy-N-[(trimethylsilyl)methyl]benzenemethanamine as a clear oil (21.5 g; >100%) in quantitative yield. The product (92% pure according to GC-MS) was used without further purification.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThen the mixture was concentrated under vacuum at 70° C. with a rotary evaporator
  3. customto remove all volatiles
  4. additionThe white residue was mixed with n-heptane (250 ml)
  5. filtrationfiltered over a glass
  6. filtrationfilter
  7. washThe salt residue was washed with n-heptane (2×25 ml)
  8. concentrationThe combined heptane filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-f3488d078fa941aa9f20f92222357155
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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