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Diisopropylcarbodiimide → (2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1H-indol-3-yl)-butyl]-amine

HRID 1290266
ノート
印刷プレビュー

反応式

HRID 1290266 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][C:15](O)=O.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:39]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[O:42][CH2:41][CH:40]1[CH2:49][NH2:50]>CN(C=O)C>[O:39]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[O:42][CH2:41][CH:40]1[CH2:49][NH:50][CH2:15][CH2:14][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochlorideHCID 112417775-Methoxyindole-3-butyric acid

生成物 1

HCID 18923900(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1H-indol-3-yl)-butyl]-amine収率 76.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

5-methoxyindole-3-butyric acid (1.5 g, 6.4 mmole), 1-hydroxybenzotriazole hydrate (1.0 g, 7.7 mmole) and 1,3-diisopropylcarbodiimide (2.4 ml, 15.4 mmole) were combined in 150 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.3 g, 6.4 mmole) in 50 ml of DMF and the mixture was further stirred for 24 hours. The solvent was removed and the residue partitioned between dichloromethane and water. The separated dichloromethane layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant. Fractions containing product were concentrated and washed with a minimum amount of TBF to remove a by-product and to give 1.8 g (74%) of the desired product, (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-4-(5-1H-indole-3-yl)-butanamide, as an oil.

後処理

  1. stirringthe mixture was further stirred for 24 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe separated dichloromethane layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on a silica gel column
  8. additionFractions containing product
  9. concentrationwere concentrated
  10. washwashed with a minimum amount of TBF
  11. customto remove a by-product

出典と根拠

ORDレコード
ord-69eabdf1c20d4ce088acdcf841e1a851
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05750724

反応ノート

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