Hydrochloric Acid → N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamine

HRID 855226ノート

反応式

HRID 855226 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].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.[BH4-].[Na+].Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 703244-tert-ButylbenzaldehydeHCID 748663-MethoxyphenethylamineHCID 4311764Sodium borohydride

生成物 1

HCID 39418093N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamine収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.22 ml of 2-(3-methoxy-phenyl)-ethylamine (1.5 mmol) were dissolved in 5 ml methanol at rt and then refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added in portions and the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 ml 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 (90 g silica gel; EtOAc/heptane 1:1) to give 520 mg light yellow oil (>100%).

後処理

  1. temperaturerefluxed for 2 h
  2. temperaturethe reaction mixture was then refluxed for 3 h
  3. temperatureAfter cooling down to rt
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with water/EtOAc
  6. customAfter separation of the organic phase
  7. extractionthe aqueous phase was extracted with EtOAc
  8. washthe combined organic phases were washed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered off
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:1)

出典と根拠

ORDレコード
ord-9e2d3240f3a345eea89d34dffa681b9f
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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