Triethylamine → HCID 86730000, compound

HRID 1483020Notes

Reaction equation

HRID 1483020 reaction equation
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4][NH2:5].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=1.C(N(CC)CC)C>C(#N)C>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[N:5][CH2:4][C:3]([F:7])([F:6])[F:2])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 86730000HCID 86730000, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,2,2-Trifluoroethylamine hydrochloride (3.98 g, 29.4 mmol) in acetonitrile (9 mL) was added 3-pyridinecarboxaldehyde (Sigma-Aldrich) (2.1 g, 19.6 mmol) followed by triethylamine (4 ml, 29.43 mmol) at 0° C. The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was filtered and the solids washed with acetonitrile. The filtrate was then concentrated in vacuo. The residue was taken up in ethyl ether, filtered and concentrated to afford 3.12 g (84%) of the tile compound as a white foam. 1H NMR (300 MHz, DMSO-d6) δ4.40 (m, 2H), 7.52 (m, 1H), 8.18 (m, 1H), 8.61 (s, 1H), 8.70 (dd, J=1.8, 4.8 Hz, 1H), 8.92 (d, J=1.8, 1H). MS (ESI, [M+H] +), 189.5.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with acetonitrile
  3. concentrationThe filtrate was then concentrated in vacuo
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5bfa95dc8d554aeba052a9b867043406
Source dataset
uspto-grants-2016_08
Patent number
US09416124B2

Reaction notes

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