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

HRID 648960Notes

Reaction equation

HRID 648960 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

Here, 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one (131.5 g, 0.6 mol) is suspended in dimethylsulfoxide (900 ml) and mixed with potassium tert.butoxide (80.8 g, 0.72 mol) with stirring. After 10 minutes, the solution obtained is added dropwise, while cooling with ice water, to 1-bromo-3-chloropropane (77 ml, 0.72 mol) in dimethylsulfoxide (300 ml). After 1 hour the mixture is poured into ice water. After a short time the greasy precipitate begins to crystalize. The precipitate is suction filtered, dissolved in acetone, precipitated with water once again, suction filtered and dried.

Workup

  1. customthe solution obtained
  2. additionis added dropwise
  3. customto crystalize
  4. filtrationfiltered
  5. dissolutiondissolved in acetone
  6. customprecipitated with water once again
  7. filtrationsuction filtered
  8. customdried

Sources & evidence

ORD record
ord-da77e7dadbc34669b8085240581b845a
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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