Iodoethane → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1-ethyltetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587097Notes

Reaction equation

HRID 587097 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26]4[NH:30][N:29]=[N:28][N:27]=4)[CH2:23][CH2:22][C:21]([C:31]([O:33][CH3:34])=[O:32])=[CH:20][C:19]=3[CH:35]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH2:42](I)[CH3:43]>C(#N)C>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26]4[N:30]([CH2:42][CH3:43])[N:29]=[N:28][N:27]=4)[CH2:23][CH2:22][C:21]([C:31]([O:33][CH3:34])=[O:32])=[CH:20][C:19]=3[CH:35]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178450548HCID 178450548, compound

Product 1

HCID 22329162Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1-ethyltetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.9 g) was dissolved in acetonitrile (190 ml). To the solution were added potassium carbonate (1.65 g) and ethyl iodide (0.76 ml), and the mixture was stirred at 50° C. for 16 hours. The solvent was concentrated to 1/3 under reduced pressure, which was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/1→1/2) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1-ethyltetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.05 g) and methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2-ethyltetetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.42 g).

Workup

  1. concentrationThe solvent was concentrated to 1/3 under reduced pressure, which
  2. additionwas added to water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/1→1/2)

Sources & evidence

ORD record
ord-7060977c8ad04cb89a429477e262b99f
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

Loading…