HCID 22990107, compound → HCID 17824062, compound

HRID 1169389Notes

Reaction equation

HRID 1169389 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 2

HCID 22990107HCID 22990107, compoundHCID 86759185HCID 86759185, compound

Product 1

HCID 17824062HCID 17824062, compoundYield 72.7%

Procedure

To N-(4-cyanomethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (200 mg) was added a solution of a 28% hydrogen chloride/ethanol/dioxane (2 ml). The resulting mixture was kept overnight in a refrigerator and then was concentrated, and ethanol (4 ml) and piperidine (1 ml) were added to the residue. After being stirred at room temperature for one hour, the reaction mixture was concentrated and was mixed with an aqueous solution of sodium bicarbonate. The mixture was extracted with ethyl acetate/methanol. The extract was dried (magnesium sulfate) and was then concentrated. To the residue was added 4 N hydrochloric acid/ethyl acetate, and the precipitate was collected by filtration and was washed with ethyl acetate to obtain N-[4-(1-piperidino)carbonimidoylmethyl]phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 46) (103 mg) as a white powder.

Workup

  1. concentrationwas concentrated
  2. additionethanol (4 ml) and piperidine (1 ml) were added to the residue
  3. concentrationthe reaction mixture was concentrated
  4. additionwas mixed with an aqueous solution of sodium bicarbonate
  5. extractionThe mixture was extracted with ethyl acetate/methanol
  6. dry with materialThe extract was dried (magnesium sulfate)
  7. concentrationwas then concentrated
  8. additionTo the residue was added 4 N hydrochloric acid/ethyl acetate
  9. filtrationthe precipitate was collected by filtration
  10. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-e456916fb1f4494bb361bda24c2c7d45
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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