Indole-3-Butyric Acid → HCID 18923893, compound

HRID 1290250Notes

Reaction equation

HRID 1290250 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13](O)=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[OH:37][C:38]1[CH:39]=[CH:40][C:41]2[O:46][CH2:45][CH:44]([CH2:47][NH2:48])[O:43][C:42]=2[CH:49]=1>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][NH:48][CH2:47][CH:44]2[CH2:45][O:46][C:41]3[CH:40]=[CH:39][C:38]([OH:37])=[CH:49][C:42]=3[O:43]2)=[CH:2]1

Participants

6

Reactant 4

HCID 8617Indole-3-Butyric AcidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189238902,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine hydrochloride

Product 1

HCID 18923893HCID 18923893, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Indolebutyric acid (1.0 g, 5.0 mmole), 1-hydroxybenzotriazole hydrate (0.8 g, 6.0 mmole) and 1,3-diisopropylcarbodiimide (1.9 ml, 12.0 mmole) were combined in 100 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 7-hydroxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.1 g, 5.0 mmole) in 50 ml of DMF and the mixture was further stirred for 24 hours. The solvent was removed and replaced with dichloromethane. The mixture was then washed with H2O. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Chromatography on silica gel using first dichloromethane and then 2.5% methanol in dichloromethane as eluants gave 0.3 g (16%) of the desired product, (7-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-methyl)-4-(1H-indol-3-yl)-butanamide, as an oil.

Workup

  1. stirringthe mixture was further stirred for 24 hours
  2. customThe solvent was removed
  3. washThe mixture was then washed with H2O
  4. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-11f8f38759314419b89248c522020b68
Source dataset
uspto-grants-1998_05
Patent number
US05750724

Reaction notes

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