Triethylamine → HCID 66591171, compound

HRID 1092520Notes

Reaction equation

HRID 1092520 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 and the resultant mixture was refluxed overnight. The reaction was cooled to room temperature and 150 mL of heptane was added. The HCl salts were removed by filtration and washed with heptane. The solvent was removed by placing under house vacuum and then high vacuum. N-(3-(Trifluoromethyl)benzyl)-1-(trimethylsilyl)methanamine was isolated by vacuum distillation (bp 70-90° C./3.2 torr): 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 HCl salts were removed by filtration
  2. washwashed with heptane
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-8bd6c7a5961a43b2bf5d285f51817553
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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