Water → 1,2-Dihydro-3-methyl-1-[6-(phthalimido)hexan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068794Notes

Reaction equation

HRID 1068794 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:13])[NH:8]3.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].O>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:13])[N:8]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 141120N-(6-Bromohexyl)phthalimideHCID 135810294HCID 135810294, compound

Product 1

HCID 211901771,2-Dihydro-3-methyl-1-[6-(phthalimido)hexan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5.20 g (30 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one in 60 ml of DMF was added, while stirring under ice-cooling, 1.44 g (36 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 15 minutes at the same temperature. To the reaction mixture was added a DMF solution (20 ml) of 9.31 g (30 mmol) of N-(6-bromohexyl)phthalimide. The mixture was stirred for 1.5 hour at 110° C. After cooling, the reaction mixture was poured into water, which was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to give 3.47 g of the desired compound (28.7%, pale brown solid). NMR(200 MHz,CDCl3) δ: 1.33-1.56(4H,m), 1.68(2H,m), 1.85(2H,m), 2.82(3H,s), 3.67(2H,t,J=7.2 Hz), 4.04(2H,t,J=7.2 Hz), 6.78(1H,d,J=7.4 Hz), 7.47(1H,d,J=8.6 Hz), 7.69(1H,dd,J=8.6,7.4 Hz), 7.67-7.76(2H,m), 7.78-7.88(2H,m).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 15 minutes at the same temperature
  4. stirringThe mixture was stirred for 1.5 hour at 110° C
  5. temperatureAfter cooling
  6. extractionwas extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Sources & evidence

ORD record
ord-3afa29fc23c54d73b8f62515e24eb93b
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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