4-Methoxybenzylamine → (6-Chloro-4-trifluoromethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine

HRID 1191205

Reaktionsgleichung

Reaktionsgleichung von HRID 1191205
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:12][C:4]1[N:3]=[C:2]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 5209682,6-Dichloro-4-(trifluoromethyl)pyridine

Produkt 1

HCID 86657407(6-Chloro-4-trifluoromethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 2,6-dichloro-4-trifluoromethyl-pyridine (5.04 g, 23.3 mmol) in pyridine (10 mL) was treated with 4-methoxybenzylamine (9.19 mL, 70.0 mmol) and heated to 110° C. for 26 h. The mixture was cooled, and pyridine (8 mL) was removed in vacuo. The remaining material was diluted with water (50 mL) and extracted twice with EtOAc (75 mL, and 50 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 115-g SEPRA Si 35 SPE column (Flow rate=35 mL/min; Eluent=EtOAc-hexanes, 1:99 for 15 min, then 1:99 to 1:9 over 40 min, 1:9 for 2 min, then 1:9 to 1:4 over 20 min) to yield (6-chloro-4-trifluoromethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine as a colorless oil, which solidified upon standing. 1H-NMR (400 MHz, CDCl3) δ: 7.26 (d, J=8.6 Hz, 2H), 6.88 (d, J=8.6 Hz, 2H), 6.77 (s, 1H), 6.44 (s, 1H), 5.21 (br. s., 1H), 4.44 (d, J=5.6 Hz, 2H), 3.80 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calculated for C14H12N2OClF3: 317.1 (M+H); Measured: 317.1.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompyridine (8 mL) was removed in vacuo
  3. additionThe remaining material was diluted with water (50 mL)
  4. extractionextracted twice with EtOAc (75 mL, and 50 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on a 115-g SEPRA Si 35 SPE column (Flow rate=35 mL/min
  8. wait1:99 to 1:9 over 40 min
  9. wait1:9 for 2 min

Quellen und Nachweise

ORD-Eintrag
ord-5c9c341b0bda44fea2121ed96a4d9313
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680098B2

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