Acetic Acid → HCID 22329115, compound

HRID 587091Notes

Reaction equation

HRID 587091 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[CH:14](=O)[CH2:15][CH3:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 223291087-Bromo-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one

Product 1

HCID 22329115HCID 22329115, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of 7-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one (5.0 g), propionaldehyde (15 ml) and acetic acid (4.7 ml) in 1,2-dichloroethane (250 ml) was added sodium triacetoxyborohydride (22.0 g) at room temperature, and the mixture was stirred for 6 hours. To the reaction system was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine, and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:4) to give 7-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one (5.89 g) as yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was separated
  6. custompurified with column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-282eb1e0f185432a99174646bddc456b
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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