Hydrochloric Acid → HCID 56996792, compound

HRID 2287882Notes

Reaction equation

HRID 2287882 reaction equation
[H-].[Na+].[CH2:3]([N:6]([CH2:20][CH2:21][CH3:22])[CH:7]1[CH2:19][C:10]2=[CH:11][C:12]3[C:13](=[O:18])[NH:14][CH2:15][C:16]=3[CH:17]=[C:9]2[CH2:8]1)[CH2:4][CH3:5].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=1.Cl>CN(C=O)C>[CH2:20]([N:6]([CH2:3][CH2:4][CH3:5])[CH:7]1[CH2:19][C:10]2=[CH:11][C:12]3[C:13](=[O:18])[N:14]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=4)[CH2:15][C:16]=3[CH:17]=[C:9]2[CH2:8]1)[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 18705870HCID 18705870, compound

Product 1

HCID 56996792HCID 56996792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
84 °C

Procedure

To a slurry of washed NaH (0.05 g, 1.32 mmol) in DMF (5 mL) was added a slurry of 6-(Dipropylamino)-3,5,6,7-tetrahydrocyclopent[f]isoindol-1(2H)-one (94, 0.30 g, 1.10 mmol) in DMF (10 mL). The slurry was heated to 84° C. and after 40 min, was treated with a solution of alpha-bromo-p-tolunitrile (0.43 g, 2.20 mmol) in DMF (10 mL). After 24 h, the reaction was quenched with H2O and extracted with CH2Cl2. The organic layers were washed with brine, dried (MgSO4), and concentrated on hi-vac. The reside was purified on silica gel, eluting with CH2Cl2 /MeOH to give an oil that was converted to an HCl salt and recrystallized to afford 133 as a white solid (m.p. 141-145° C.).

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with CH2Cl2
  3. washThe organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated on hi-vac
  6. customThe reside was purified on silica gel
  7. washeluting with CH2Cl2 /MeOH
  8. customto give an oil that
  9. customrecrystallized

Sources & evidence

ORD record
ord-db025aa3e07246cd948fd13f748246f3
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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