Triethylamine → 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione

HRID 863695Notes

Reaction equation

HRID 863695 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32]([OH:34])=[O:33])=[CH:23]1.C(N(CC)CC)C>ClCCl>[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([C:31]1([C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:22]([CH3:21])[CH:23]=3)[CH2:2][C:1](=[O:5])[O:34][C:32]1=[O:33])=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 11116734HCID 11116734, compound

Product 1

HCID 196963163-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dioneYield 22.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.5 g of oxalyl chloride were added dropwise to an ice-cold solution of 2.0 g of 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole (J. Org. Chem. 33, 1968, 4286) in 50 ml of dichloromethane. The mixture was stirred for 2 hours. The solvent was removed in a vacuum and the residue was dissolved in dichloromethane. The solution obtained was added to a solution of 2.2 g of 1-methyl-3-indolylacetic acid and 2.73 g of triethylamine in 50 ml of dichloromethane. The mixture was stirred and then concentrated. The residue was chromatographed on silica gel with dichloromethane and there was obtained 1.0 g of 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione of melting point 257°-259° C.

Workup

  1. customThe solvent was removed in a vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customThe solution obtained
  4. stirringThe mixture was stirred
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with dichloromethane

Sources & evidence

ORD record
ord-b40e585f1f6b4f499d8db2815a94f907
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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