Benzylamine → 2-Benzyl-1-(4-(trifluoromethyl)phenyl)-1,2-dihydroisoquinolin-3(4H)-one

HRID 445315

Reaktionsgleichung

Reaktionsgleichung von HRID 445315
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:13]([N:20]1[C:28](=[O:29])[CH2:27][C:21]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 5

HCID 7504BenzylamineHCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 679964-(Trifluoromethyl)benzaldehyde

Produkt 1

HCID 595363842-Benzyl-1-(4-(trifluoromethyl)phenyl)-1,2-dihydroisoquinolin-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(Trifluoromethyl)benzaldehyde (1.87 mL, 14.0 mmol) and benzylamine (1.53 mL, 14.0 mmol) were dissolved into 40 mL of DCM and 4 Å molecular sieve was added. The mixture was left under nitrogen for 3 days. Molecular sieve was removed via filtration. 25 mL of DCM was used to wash the filter cake. To the filtrate, phenylacetyl chloride (1.90 mL, 14.4 mmol) was added and the pale yellow solution was stirred for 2 h. Then trifluoromethanesulfonic acid (6.20 mL, 70.1 mmol) was added. The mixture was stirred for 1.5 h then poured into a mixture of ice (˜100 mL) and 5N sodium hydroxide (˜50 mL). The phases were separated and the aqueous phase was extracted with DCM. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes) twice to afford the title compound as a light yellow semi-solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.56-7.74 (m, 4H) 7.41 (d, J=6.87 Hz, 1H) 7.13-7.33 (m, 8H) 5.80 (s, 1H) 5.30 (d, J=15.20 Hz, 1H) 3.81-4.01 (m, 2H) 3.66-3.78 (m, 1H).

Aufarbeitung

  1. additionwas added
  2. customMolecular sieve was removed via filtration
  3. washto wash the filter cake
  4. stirringThe mixture was stirred for 1.5 h
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with DCM
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford a yellow oil
  11. customThe crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes) twice

Quellen und Nachweise

ORD-Eintrag
ord-00b4e0bea38147e09376e1d0aebc8930
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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