Hydrochloric Acid → (3,5-Bis-trifluoromethyl-benzyl)-methyl-(3-o-tolyl-pyridin-4-ylmethyl)-amine

HRID 1975958ノート

反応式

HRID 1975958 の反応式
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH3:23])[C:8](=O)[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].Cl.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1.CCOCC>[F:29][C:27]([F:28])([F:30])[C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:26]=1)[CH2:6][N:7]([CH3:23])[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9846661N-(3,5-bis(trifluoromethyl)benzyl)-N-methyl-3-o-tolylisonicotinamide

生成物 1

HCID 86756660(3,5-Bis-trifluoromethyl-benzyl)-methyl-(3-o-tolyl-pyridin-4-ylmethyl)-amine収率 258.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 0.12 g (0.265 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-3-o-tolyl-isonicotinamide in 3 ml tetrahydrofuran 1.6 ml of a 1M solution of BH3 in tetrahydrofuran was added and the reaction mixture stirred for 16 h at 60° C. After addition of 2 ml 3M HCl in ether the reaction mixture was stirred for 3 h at 60° C. The solution was cooled to room temperature and 5 ml 3N sodium hydroxide solution and 10 ml ethyl acetate were added. Stirring was continued for ½ h, the phases separated and the aqueous phase extracted twice with 15 ml ethyl acatate. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.30 g (25%) of the title compound as a pale yellow oil.

後処理

  1. stirringwas stirred for 3 h at 60° C
  2. temperatureThe solution was cooled to room temperature
  3. stirringStirring
  4. waitwas continued for ½ h
  5. customthe phases separated
  6. extractionthe aqueous phase extracted twice with 15 ml ethyl acatate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated

出典と根拠

ORDレコード
ord-f5e4b20a80f54e3b96babfc23aa4bd9c
出典データセット
uspto-grants-2001_05
特許番号
US06225316B1

反応ノート

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