Triethylamine → HCID 66591171, compound

HRID 2363498Notes

Reaction equation

HRID 2363498 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-6cba676b7d9b4d8e921ad76eb96852e3
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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