Ethylenediamine → HCID 9845190, compound

HRID 1169438Notes

Reaction equation

HRID 1169438 reaction equation
Cl.C(O[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH2:17][CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:15])=[CH:9][CH:8]=1)=[NH:6])C.[CH2:34](N)[CH2:35][NH2:36]>C(O)C>[NH:6]1[CH2:34][CH2:35][N:36]=[C:5]1[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH2:17][CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 17823976HCID 17823976, compound

Product 1

HCID 9845190HCID 9845190, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a solution of N-[4-(ethoxycarbonimidoyl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide hydrochloride (200 mg) in ethanol (4 ml) was added ethylenediamine (0.09 ml). The resulting mixture was stirred at room temperature overnight, was then concentrated and was mixed with an aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate/tetrahydrofuran, and the extract was washed with an aqueous solution of sodium chloride. The extract was dried (anhydrous magnesium sulfate) and was then concentrated, and the residue was recrystallized from ethyl acetate/methanol to obtain N-[4-(2-imidazolin-2-yl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 92) (60 mg) as colorless crystals.

Workup

  1. concentrationwas then concentrated
  2. additionwas mixed with an aqueous solution of sodium bicarbonate
  3. extractionThe resulting mixture was extracted with ethyl acetate/tetrahydrofuran
  4. washthe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialThe extract was dried (anhydrous magnesium sulfate)
  6. concentrationwas then concentrated
  7. customthe residue was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-a993b874ee894fe2a5af6432f9a41438
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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