Benzylamine → N-Benzyl-1-tert-butyl-1,1-diphenylsilanamine

HRID 256889Notes

Reaction equation

HRID 256889 reaction equation
[C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17]>C(#N)C>[Si:20]([NH:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14007724N-Benzyl-1-tert-butyl-1,1-diphenylsilanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzenemethanamine (21.8 mL, 0.20 mol) and triethylamine (41.2 mL, 0.30 mol) in acetonitrile (400 mL) was added dropwise t-butylchlorodiphenylsilane (52 mL, 0.20 mol). The mixture was stirred at room temperature for 3 hours 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 a 4:1 mixture of ether/hexane and washed sequentially with H2O, saturated NaHCO3 solution and H2O. The solution was dried (Na2SO4 /K2CO3) and concentrated to leave an oil which was distilled under high vacuum. The major fraction consisting of the pure product (45.9 g, 66%) distilled from 140° to 160° C. at about 0.1-0.2 mm Hg and crystallized on standing at room temperature, m.p. 34°-36° C.

Workup

  1. filtrationfiltered
  2. customto remove the insoluble white precipitate (triethylamine hydrochloride)
  3. customAfter removal of the solvent in vacuo
  4. additionthe crude product was taken up in a 4:1 mixture of ether/hexane
  5. washwashed sequentially with H2O, saturated NaHCO3 solution and H2O
  6. dry with materialThe solution was dried (Na2SO4 /K2CO3)
  7. concentrationconcentrated
  8. customto leave an oil which
  9. distillationwas distilled under high vacuum
  10. distillationdistilled from 140° to 160° C. at about 0.1-0.2 mm Hg
  11. customcrystallized
  12. customon standing at room temperature

Sources & evidence

ORD record
ord-267badf95ac146a4b4537f225531a571
Source dataset
uspto-grants-1993_11
Patent number
US05260309

Reaction notes

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