Triethylamine → (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamide

HRID 428129

反応式

HRID 428129 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](/[CH:23]=[CH:24]/[C:25](O)=[O:26])[CH:18]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)[C:25](=[O:26])/[CH:24]=[CH:23]/[C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 138365N-MethylmescalineHCID 516892Sodium BicarbonateHCID 776396trans-3-(3-Pyridyl)acrylic acid

生成物 1

HCID 23067296(E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamide収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-Methyl-3,4,5-trimethoxyphenethylamine (1.60 g, 7.11 mmol) and trans-3-(3-pyridyl)acrylic acid (1.17 g) were dissolved in dimethylformamide (8 ml), and diethylphosphoric cyanide (1.3 ml) and triethylamine (2.2 ml) were sequentially added under ice-cooling and stirring and stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the reaction mixture was extracted with dichloromethane, washed with water and dried over potassium carbonate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1) to yield amorphous (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenoic acid amide (2.37 g, 94%). Then, hydrogen chloride-methanol was added to the product (1.80 g) to produce its hydrochloride, which was recrystallized in a mixed solvent of ethyl acetate-methanol to yield the titled compound (1.59 g, 57%).

後処理

  1. temperaturecooling
  2. stirringstirred at room temperature for 1 hour
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over potassium carbonate
  6. distillationThe solvent was distilled out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1)

出典と根拠

ORDレコード
ord-c2f9a2806f274d10848e86d2d0cd1129
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

関連ノート

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