Chlorotrimethylsilane → Silanamine, N-(phenylmethyl)-N,1,1,1-tetramethyl-

HRID 1192998Notes

Reaction equation

HRID 1192998 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C(OCC)C>[CH3:17][Si:16]([CH3:19])([CH3:18])[N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7669N-MethylbenzylamineHCID 178418339Butyllithium

Product 1

HCID 26949Silanamine, N-(phenylmethyl)-N,1,1,1-tetramethyl-Yield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Step 1—To a stirring solution of N-methylbenzylamine (100 ml, 93.9 g, 0.77 mol) in diethyl ether (500 ml) cooled at −78° C. was added n-butyl lithium (2.4 M in hexanes, 355 ml, 0.85 mol) keeping the temperature below −60° C. The resulting slurry was stirred for 1 hour then chlorotrimethylsilane (118 ml, 0.93 mol) was added while keeping the temperature below −70° C. The reaction was allowed to warm to room temperature overnight then filtered to remove the precipitated white solid. The filtrates were concentrated in vacuo then distilled under high-vacuum to yield the N-trimethylsilyl-N-methylbenzylamine (102 g, 94%) as a colorless liquid: b.p. 54° C./0.5 mmHg; 1H NMR (CDCl3) 0.19 (s, 9H), 2.37 (s, 3H), 3.90 (2, 2H) 7.22-7.39 (m, 5H)

Workup

  1. customthe temperature below −60° C
  2. customthe temperature below −70° C
  3. filtrationthen filtered
  4. customto remove the precipitated white solid
  5. concentrationThe filtrates were concentrated in vacuo
  6. distillationthen distilled under high-vacuum

Sources & evidence

ORD record
ord-a6f88159b7ac4f818f99b256bc09ddc0
Source dataset
uspto-grants-2014_03
Patent number
US08680332B2

Reaction notes

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