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

HRID 570220

反応式

HRID 570220 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f7b44062cd4471c994c2dde409a58b9
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

関連ノート

読み込み中…