HCID 22990107, compound → HCID 17824062, compound

HRID 1169440Notes

Reaction equation

HRID 1169440 reaction equation
C(CC1C=CC([NH:10][C:11]([C:13]2[CH2:14][CH2:15][O:16][C:17]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)=[CH:20][C:18]=3[CH:19]=2)=[O:12])=CC=1)#N>Cl.C(O)C.O1CCOCC1>[CH3:30][C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:22]=[CH:23][C:17]3[O:16][CH2:15][CH2:14][C:13]([C:11]([NH2:10])=[O:12])=[CH:19][C:18]=3[CH:20]=2)=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 22990107HCID 22990107, compound

Product 1

HCID 17824062HCID 17824062, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 86759185HCID 86759185, compoundSolvent

Procedure

To N-(4-cyanomethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (789 mg) was added under ice cooling a solution of 24% hydrogen chloride/ethanol/dioxane (10 ml). The resulting mixture was stirred at room temperature for one hour and was then concentrated. To the residue suspended in ethanol (20 ml) was added ethylenediamine (0.4 ml) under ice cooling. The resulting mixture was stirred at room temperature for 15 hours, was then concentrated and was mixed with an aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate, and the extract was washed with an aqueous solution of sodium chloride. After drying (magnesium sulfate), the extract was concentrated, and the residue was recrystallized from ethyl acetate/methanol to obtain N-(4-imidazolin-2-yl)methyl]phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 94) (580 mg) as colorless crystals.

Workup

  1. concentrationwas then concentrated
  2. additionwas added ethylenediamine (0.4 ml) under ice cooling
  3. stirringThe resulting mixture was stirred at room temperature for 15 hours
  4. concentrationwas then concentrated
  5. additionwas mixed with an aqueous solution of sodium bicarbonate
  6. extractionThe resulting mixture was extracted with ethyl acetate
  7. washthe extract was washed with an aqueous solution of sodium chloride
  8. dry with materialAfter drying (magnesium sulfate)
  9. concentrationthe extract was concentrated
  10. customthe residue was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-73a09b03816d4121b6a8617d32df83fc
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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