Hydrochloric Acid → (4-Tert-butyl-2-chloro-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amine

HRID 855256ノート

反応式

HRID 855256 の反応式
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=O)=[C:7]([Cl:27])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[C:7]([Cl:27])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 695134924-tert-butyl-2-chloro-N-[2-(3-trifluoromethoxy-phenyl)-ethyl]-benzamide

生成物 1

HCID 69343329(4-Tert-butyl-2-chloro-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amine収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.60 ml (0.60 mmol) of a 1M borane-THF complex solution in THF were added under nitrogen at rt to 80 mg (0.20 mmol) of 4-tert-butyl-2-chloro-N-[2-(3-trifluoromethoxy-phenyl)-ethyl]-benzamide dissolved in 1 ml THF. The reaction mixture was heated to reflux over night. At rt 2 ml 2N aqueous HCl solution were added and the reaction mixture was heated to reflux for 3 h. The reaction mixture was basified with 3 ml 2N aqueous NaOH solution and extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (25 g silica gel; DCM/methanol 19:1) to yield 60 mg (78%) (4-tert-butyl-2-chloro-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amine as a colorless oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.40-7.19 (m, 7H), 3.74 (s, 2H), 2.78 (s, 4H), 1.26 (s, 9H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux over night
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 3 h
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic layers were washed with saturated aqueous NaCl solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography (25 g silica gel; DCM/methanol 19:1)

出典と根拠

ORDレコード
ord-dc738d586a9a4db08d6ba55c191166af
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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