1-Phenethylamine → HCID 357665, compound

HRID 256891Notes

Reaction equation

HRID 256891 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:3].C(N(CC)CC)C.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[Si:21]([NH:3][CH:2]([CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 74081-PhenethylamineHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 357665HCID 357665, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of racemic α-methyl-benzenemethanamine (24.2 g, 0.2 mol) and triethylamine (42 mL, 0.30 mol) in acetonitrile (400 mL) in a flame-dried flask under nitrogen was added dropwise t-butylchlorodiphenylsilane (47 mL, 0.18 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 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 pure title compound (30.5 g, 47%) distilled from 160° to 165° C. at about 0.4 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 160° to 165° C. at about 0.4 mm Hg

Sources & evidence

ORD record
ord-d9de7a1fd1f449e3803e42dce31ec81a
Source dataset
uspto-grants-1993_11
Patent number
US05260309

Reaction notes

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