Acetic Acid → methyl 7-bromo-1-butyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586917Notes

Reaction equation

HRID 586917 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[C:17](O)(=O)[CH3:18].[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:22].[Na+].C(=O)([O-])O.[Na+]>CCOCCOC1C=CC(C2C=CC3N(C=O)CCC(C(NC4C=CC(CN(C)C5CCOCC5)=CC=4)=O)=CC=3C=2)=CC=1F.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:21][CH2:22][CH2:17][CH3:18])[CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22329329methyl 7-bromo-1-butyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22329144HCID 22329144, compoundSolvent

Procedure

In 1,2-dichloroethane (20) were dissolved methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.0 g), n-butylaldehyde (1.3 ml) and acetic acid (0.41 ml), and to the solution was added sodium triacetoxyborohydride (3.8 g). The mixture was stirred at room temperature overnight, poured into water, neutralized with sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-bromo-1-butyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.9 g) as pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6096d3a84de94e6298e7547120acbc10
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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