Water → HCID 21190165, compound

HRID 619524Notes

Reaction equation

HRID 619524 reaction equation
[N:1]1[CH:2]=[C:3]2[NH:11][C:10](=[O:12])[C:5]3=[CH:6][CH:7]=[CH:8][C:9]=1[N:4]23.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].O>CN(C=O)C>[C:22]1(=[O:31])[N:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]2[C:3]3=[CH:2][N:1]=[C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([N:4]34)[C:10]2=[O:12])[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 136770N-(5-Bromopentyl)phthalimideHCID 13809154HCID 13809154, compound

Product 1

HCID 21190165HCID 21190165, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 81 mg (0.51 mmol) of 3,4-dihydro-1,3,7b-triazacyclopent[cd]inden-4-one in 1 ml of DMF was added, while stirring under ice-cooling, 25 mg (0.63 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 solution of 151 mg (0.51 mmol) of N-(5-bromopentyl)phthalimide in 1 ml of DMF. The mixture was stirred for two hours at 110° C. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate. The extract was washed with an aqueous saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 40 mg of the desired compound (20.9%, a colorless solid).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 15 minutes at the same temperature
  4. stirringThe mixture was stirred for two hours at 110° C
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with an aqueous saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Sources & evidence

ORD record
ord-1d9a98338e9e4c2f8ca85e03e411b4fb
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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