Lysergic Acid → (+)-Lysergic acid diethylamide

HRID 1372350

反応式

HRID 1372350 の反応式
[OH:1][C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=O.[C:21](C1NC=CN=1)([C:23]1[NH:24][CH:25]=[CH:26]N=1)=O.C(NCC)C>CN(C)C=O>[CH2:23]([N:24]([CH2:25][CH3:26])[C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=[O:1])[CH3:21]

参加物

5

反応物 3

HCID 6717Lysergic AcidHCID 8021DiethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

生成物 1

HCID 5761(+)-Lysergic acid diethylamide収率 75.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 10.0 g (0.037 mol) of d-lysergic acid in 500 ml of dry dimethyl formamide (DMF), under argon, was treated with 9.0 g of carbonyl diimidazole and stirred at room temperature for 1 hour The reaction was then treated with 38 ml of diethylamine and stirred at room temperature overnight. The reaction was concentrated under reduced pressure. The residue was taken up in 500 ml of methylene chloride and washed with 500 ml of water. Insoluble material was removed by filtration and the layers were separated. The organic portion was washed with 250 ml of saturated brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on 800 g of silica gel using 3% methanol in methylene chloride to yield 9.0 g (75%) of d-lysergic acid diethylamide (LSD) as a light brown amorphous solid after evaporation of the solvents.

後処理

  1. stirringstirred at room temperature overnight
  2. concentrationThe reaction was concentrated under reduced pressure
  3. washwashed with 500 ml of water
  4. customInsoluble material was removed by filtration
  5. customthe layers were separated
  6. washThe organic portion was washed with 250 ml of saturated brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on 800 g of silica gel using 3% methanol in methylene chloride

出典と根拠

ORDレコード
ord-2d62b475dedc473eba0418467538045b
出典データセット
uspto-grants-2007_01
特許番号
US07157560B2

関連ノート

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