4-tert-Butylbenzaldehyde → (4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

HRID 19781

反応式

HRID 19781 の反応式
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][NH2:23])[CH:17]=[CH:18][C:19]=1[Cl:20].[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 703244-tert-ButylbenzaldehydeHCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydride

生成物 1

HCID 68563688(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine収率 102.1%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒

実験手順

0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.227 ml 2-(3,4-dichloro-phenyl)-ethylamine (1.5 mmol) were dissolved in 4.5 ml methanol at RT, and after stirring for 30 min at RT, were refluxed for 2 h. After cooling down to RT, 85 mg (2.25 mmol) sodium borohydride were added and after stirring for 5 min at RT, the reaction mixture was then refluxed for 2 h. After cooling down to RT, the reaction mixture was treated with 4 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2) to give 515 mg colorless viscous oil (97%). MS (ISP) 336.2 (M+H)+.

後処理

  1. temperaturewere refluxed for 2 h
  2. temperatureAfter cooling down to RT
  3. stirringafter stirring for 5 min at RT
  4. temperaturethe reaction mixture was then refluxed for 2 h
  5. temperatureAfter cooling down to RT
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2)

出典と根拠

ORDレコード
ord-a189fa60b3d0427fa29e1260ede59189
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

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