Triethylamine → HCID 14772825, compound

HRID 256893Notes

Reaction equation

HRID 256893 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18]([Si:22](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[Si:22]([NH:9][CH:8]([CH3:10])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 1230631-(4-Fluorophenyl)ethylamine

Product 1

HCID 14772825HCID 14772825, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of racemic 4-fluoro-α-methylbenzenemethanamine (2.95 g, 21.2 mmol) and triethylamine (4.3 mL, 30.9 mmol) in acetonitrile (75 mL) in a flame-dried flask under nitrogen was added dropwise t-butylchlorodiphenylsilane (5.5 mL, 21.1 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 pure title compound (3.8 g, 47%) distilled from 123° to 143° C. at 0.15 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 123° to 143° C. at 0.15 mm Hg

Sources & evidence

ORD record
ord-a676f5749d134f3099e3b5f79b1a51df
Source dataset
uspto-grants-1993_11
Patent number
US05260309

Reaction notes

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