Acetonitrile → N-t-Butyldiphenylsilyl-alpha,4-dimethyl-benzenemethanamine

HRID 256895Notes

Reaction equation

HRID 256895 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8]([Si:12](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])([CH3:10])[CH3:9].[C:26](#N)[CH3:27]>>[Si:12]([NH:3][CH:6]([CH3:7])[C:13]1[CH:18]=[CH:17][C:26]([CH3:27])=[CH:15][CH:14]=1)([C:8]([CH3:11])([CH3:10])[CH3:9])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14772826N-t-Butyldiphenylsilyl-alpha,4-dimethyl-benzenemethanamine

Procedure

To a solution of racemic α,4-dimethyl-benemethanamine (4.00 g, 30.0 mmol) and triethylamine (6.1 mL, 43.8 mmol) in acetonitrile (100 mL) in a flame-dried flask under nitrogen was added dropwise t-butylchlorodiphenylsilane (7.7 mL, 29.6 mmol). The mixture was stirred at room temperature overnight and then filtered to remove the insoluble white precipitate (triethylamine hydrochloride). After removal of the solvent in vacuo, the crude product was taken up in ether and washed sequentially with H2O, saturated NaHCO3 solution and brine. The solution was dried (Na2SO4 /K2CO3) and concentrated to leave a clear oil which was distilled under high vacuum. The major fraction consisting of the title compound (6.7 g, 60%) distilled from 134° to 165° C. at 0.1 mm Hg.

Workup

  1. filtrationfiltered
  2. customto remove the insoluble white precipitate (triethylamine hydrochloride)
  3. customAfter removal of the solvent in vacuo
  4. washwashed sequentially with H2O, saturated NaHCO3 solution and brine
  5. dry with materialThe solution was dried (Na2SO4 /K2CO3)
  6. concentrationconcentrated
  7. customto leave a clear oil which
  8. distillationwas distilled under high vacuum
  9. distillationdistilled from 134° to 165° C. at 0.1 mm Hg

Sources & evidence

ORD record
ord-0be5e62d86d34353ac0fcc3a9d3953d0
Source dataset
uspto-grants-1993_11
Patent number
US05260309

Reaction notes

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