Sodium Hydroxide → 3,4-Dimethoxybenzenepropanamine

HRID 458781ノート

反応式

HRID 458781 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH2:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[H-]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][NH2:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 8833563-(3,4-Dimethoxyphenyl)propanamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 22810533,4-Dimethoxybenzenepropanamine収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 3-(3,4-dimethoxy-phenyl)--propionamide (11.09 g, 53.00 mmol) in anhydrous THF (400 ml) was slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106.00 mmol) in anhydrous THF (170 ml). Upon completion of the addition, the mixture was stirred at reflux for 2 h. After cooling to 0° C., H2O (5 ml) and NaOH 1N (5 ml) were added dropwise to decompose the excess of hydride. The suspension was then filtered and the residue after evaporation was partitioned between H2O (40 ml) and CH2Cl2 (100 ml). The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the crude amine (7.00 g, 35.84 mmol, 68%) as a yellow oil.

後処理

  1. temperaturecooled
  2. additionUpon completion of the addition
  3. temperatureat reflux for 2 h
  4. filtrationThe suspension was then filtered
  5. customthe residue after evaporation
  6. customwas partitioned between H2O (40 ml) and CH2Cl2 (100 ml)
  7. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-872cbc1500214608914232b174f0ee3a
出典データセット
uspto-grants-2007_03
特許番号
US07192950B2

反応ノート

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