Triethylamine → HCID 66591171, compound

HRID 1667116Notes

Reaction equation

HRID 1667116 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH2:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CCCCCCC>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][NH:10][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75361Silane, (chloromethyl)trimethyl-HCID 759623-(Trifluoromethyl)benzylamine

Product 1

HCID 66591171HCID 66591171, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

(3-(Trifluoromethyl)phenyl)methanamine (25 g, 143 mmol), (chloromethyl)trimethylsilane (19.92 mL, 143 mmol), and triethylamine (23.87 mL, 171 mmol) were combined neat. The resultant reaction mixture was refluxed overnight. The reaction was cooled to room temperature, and heptane (150 mL) was added. The HCl salts were removed by filtration, washing with heptane. The solvent was removed under reduced pressure, and the product was isolated by vacuum distillation (bp 70-90° C./3.2 torr) to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.59 (s, 1H), 7.53-7.38 (m, 3H), 3.86 (s, 2H), 2.04 (s, 2H), 1.34 (s, 1H), 0.06 (s, 9H).

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed overnight
  3. customThe HCl salts were removed by filtration
  4. washwashing with heptane
  5. customThe solvent was removed under reduced pressure
  6. customthe product was isolated by vacuum distillation (bp 70-90° C./3.2 torr)

Sources & evidence

ORD record
ord-cf873163dff34479ab9e2e3465430f5e
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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