Water → HCID 21190120, compound

HRID 619489Notes

Reaction equation

HRID 619489 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][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.O>CN(C=O)C>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][N:8]2[C:9]3[N:5]4[C:4](=[N:3][C:2]([CH3:1])=[C:6]4[C:7]2=[O:13])[CH:12]=[CH:11][CH:10]=3)[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 1358102941,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-one

Product 1

HCID 21190120HCID 21190120, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 735 mg (4.24 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one in 15 ml of DMF was added, while stirring under ice-cooling, 187 mg (4.68 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 20 minutes at the same temperature. To the mixture was added a solution of 1.18 g (4.24 mmol) of 4-bromomethyl-1-tert-butoxycarbonylpiperidine in 5 ml of DMF. The mixture was stirred for one hour at 100° C. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to give 988 mg of the desired compound (62.8%, pale yellow solid).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 20 minutes at the same temperature
  4. stirringThe mixture was stirred for one hour at 100° C
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water and brine
  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)

Sources & evidence

ORD record
ord-b324e46ba23f414e9c5c7c6ba587b8d3
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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