1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

HRID 2290215Notes

Reaction equation

HRID 2290215 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.CC(C)([O-])C.[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>CS(C)=O>[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[N:9]([CH2:24][CH2:25][CH2:26][Cl:27])[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 130925033-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

An amount of 131.5 gm (0.6 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is suspended in 900 ml of dimethylsulfoxide and mixed with 80.8 gm (0.72 mol) of potassium tert.butoxide, with stirring. After ten minutes the solution obtained is added dropwise to 77 ml (0.72 mol) of 1-bromo-3-chloropropane in 300 ml of dimethylsulfoxide, while the mixture is cooled with ice water. After one hour, it is poured onto ice water, and shortly afterwards the greasy precipitate starts to crystallize. The precipitate is subjected to suction filtration, dissolved in acetone, precipitated again with water, subjected to suction filtration, and dried.

Workup

  1. customAfter ten minutes the solution obtained
  2. additionit is poured onto ice water
  3. customto crystallize
  4. filtrationThe precipitate is subjected to suction filtration
  5. dissolutiondissolved in acetone
  6. customprecipitated again with water
  7. filtrationsubjected to suction filtration
  8. customdried

Sources & evidence

ORD record
ord-125d83fd0ce740c0a586b253c4f71c64
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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