Triethylamine → alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 486371ノート

反応式

HRID 486371 の反応式
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.C(N(CC)CC)C.[BH4-].[Na+]>CO>[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 665812,3-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochloride

生成物 1

HCID 14719553alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol収率 75.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

α-Aminomethyl-3,4-dimethoxybenzyl alcohol hydrochloride (5.84 g, 25 mmol) was suspended in methanol (30 ml). 2,3-Dimethoxybenzaldehyde (5 g, 30 mmol) was added to the suspension and then triethylamine (3.83 ml, 27.5 mmol) was added dropwise thereto under stirring at room temperature. The resultant solution was heated under reflux for 30 minutes and then sodium borohydride (1.4 g, 37 mmol) was slowly added thereto under stirring under cooling with ice. After the completion of foaming, the solvent was distilled off under reduced pressure. Water was added to the residue, which was made acidic with 3N hydrochloric acid and washed with ether. The cistern was made basic with aqueous ammonia and then subjected to extraction with dichloromethane. The dichloromethane layer was washed with water and then a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant crystals were washed with isopropyl ether to obtain 6.56 g of α-[[(2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol.

後処理

  1. temperatureunder reflux for 30 minutes
  2. stirringunder stirring
  3. temperatureunder cooling with ice
  4. distillationAfter the completion of foaming, the solvent was distilled off under reduced pressure
  5. additionWater was added to the residue, which
  6. washwashed with ether
  7. extractionsubjected to extraction with dichloromethane
  8. washThe dichloromethane layer was washed with water
  9. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. washthe resultant crystals were washed with isopropyl ether

出典と根拠

ORDレコード
ord-2b0affc108d848d6befc48b531f755e8
出典データセット
uspto-grants-1994_03
特許番号
US05292521

反応ノート

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