Hydrazine → 1-[6-(Amino)hexyl]-1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068798Notes

Reaction equation

HRID 1068798 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:30])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O.NN>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:8]1[C:9]2[N:5]3[C:4](=[N:3][C:2]([CH3:1])=[C:6]3[C:7]1=[O:30])[CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 211901771,2-Dihydro-3-methyl-1-[6-(phthalimido)hexan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 211900871-[6-(Amino)hexyl]-1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2.94 g (7.31 mmol) of 1,2-dihydro-3-methyl-1-[6-(phthalimido)hexan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one in 80 ml of ethanol was added 1.10 g (22.0 mmol) of hydrazine.monohydrate. The mixture was heated for 2 hours under reflux. After cooling, the resulting precipitates were filtered off. The filtrate was concentrated to give the residue, water was added, extracted with chloroform (three times). The extract was dried over anhydrous magnesium sulfate, then the solvent was distilled off to give 1.50 g of the desired compound (75.4%, pale yellow solid).

Workup

  1. temperatureThe mixture was heated for 2 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated
  7. customto give the residue, water
  8. additionwas added
  9. extractionextracted with chloroform (three times)
  10. dry with materialThe extract was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8903d6a735774f0ba3facd16d01ebc62
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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