Propanal → 7-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 587093Notes

Reaction equation

HRID 587093 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[NH:24][CH2:23][CH2:22][C:21]([C:25]([O:27]C)=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH:30](=O)[CH2:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[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]([CH2:30][CH2:31][CH3:32])[CH2:23][CH2:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 527PropanalHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 22328987methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 114301667-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.0 g, 2.53 mmol) and propionaldehyde (1 ml, 13.86 mmol) in 1,2-dichloroethane (30 ml) was added sodium triacetoxyborohydride (1.9 g, 8.96 mmol) at room temperature, and the mixture was stirred for 24 hours. To the reaction system was added 1N sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was dissolved in THF (50 ml) and methanol (50 ml), and to the solution was added 1N sodium hydroxide solution. After heating to reflux for 1 hour, the mixture was concentrated under reduced pressure. To the residue was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the resulting crystals were collected by filtration to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.895 g) as yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. dissolutionthe residue was dissolved in THF (50 ml)
  6. additionmethanol (50 ml), and to the solution was added 1N sodium hydroxide solution
  7. temperatureAfter heating
  8. temperatureto reflux for 1 hour
  9. concentrationthe mixture was concentrated under reduced pressure
  10. additionTo the residue was added 1N hydrochloric acid
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried with magnesium sulfate
  14. concentrationAfter concentration under reduced pressure
  15. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-eeeacf0d7d9947b68a1ff6799868c9fe
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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