3,5-Bis(trifluoromethyl)benzylamine → N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

HRID 2075057

Reaktionsgleichung

Reaktionsgleichung von HRID 2075057
[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2[CH:10]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:27][NH2:28].[BH4-].[Na+]>C(O)C>[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][C:9]=2[CH2:10][NH:28][CH2:27][C:26]2[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=[C:24]([C:23]([F:22])([F:36])[F:37])[CH:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4311764Sodium borohydrideHCID 589686992-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 58968615N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde (107 my, 0.36 mmol) and 3,5-bistrifluoromethylbenzylamine (113.8 mg, 0.37 mmol) in ethanol was stirred at room temperature overnight. Sodium borohydride (16.5 mg, 0.44 mmol) was added and the mixture was stirred at room temperature overnight. Solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+S Biotage silica column (eluted with 0-15% ethyl acetate in heptane) to afford the title compound (150 mg, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 0.94-1.23 (m, 6H) 1.51-1.59 (m, 1H) 1.62 (d, J=7.05 Hz, 2H) 1.69-1.78 (m, 1H) 1.99 (d, J=12.45 Hz, 1H) 3.17 (s, 3H) 3.83 (d, J=12.86 Hz, 1H) 3.92 (d, J=12.86 Hz, 1H) 4.00 (d, J=6.64 Hz, 2H) 4.22 (d, J=7.05 Hz, 1H) 7.50 (d, J=8.30 Hz, 1H) 7.55 (d, J=7.88 Hz, 1H) 7.63 (s, 1H) 7.80 (s, 1H) 7.86 (s, 2H). MS (ES30) Calc: 527.2, Found: 528.5 (M+1).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customSolvent was removed
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography over 25+S Biotage silica column (eluted with 0-15% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-fa37a9af764d4678b2b834760704c7a8
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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