Diisopropylcarbodiimide → [3-(5-Benzyloxy-1H-indol-3-yl)-propyl]-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amine

HRID 1290251Notes

Reaction equation

HRID 1290251 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][C:20](O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:44]1[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2[O:47][CH2:46][CH:45]1[CH2:54][NH2:55]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][CH2:20][NH:55][CH2:54][CH:45]1[O:44][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2[O:47][CH2:46]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochlorideHCID 189238923-[5-(Benzyloxy)-3-indolyl]propanoic Acid

Product 1

HCID 18923881[3-(5-Benzyloxy-1H-indol-3-yl)-propyl]-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amineYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Benzyloxyindole-3-propionic acid (2.7 g, 9.1 mmole), 1-hydroxybenzotriazole hydrate (1.5 g, 10.9 mmole) and 1,3-diisopropylcarbodiimide (3.4 ml, 21.8 mmole) were combined in 200 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 (1.8 g, 9.1 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. The residue was chromatographed on silica gel using first dichloromethane and then 2.5% methanol in dichloromethane as eluants to give 3.2 g (79%) of the desired product, (2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-(5-benzyloxy-1H-indol-3-yl)-propanamide, as a light tan solid.

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
  7. customThe residue was chromatographed on silica gel using first dichloromethane

Sources & evidence

ORD record
ord-68afc7d164e14007b867baf8b484e9c6
Source dataset
uspto-grants-1998_05
Patent number
US05750724

Reaction notes

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