Water → 3-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 1154681Notes

Reaction equation

HRID 1154681 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][CH2:10][CH2:11][C:5]=2[CH:4]=1.CC(C)([O-])C.[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27].O>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])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 114017697,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.1 gm (0.005 mol) of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one were suspended in 15 ml of absolute dimethylsulfoxide, and the suspension was mixed with 0.67 gm (0.006 mol) of potassium tert. butoxide, while stirring. After 10 minutes, the suspension thus obtained was added dropwise to 0.64 ml (0.006 mol) of 1-bromo-3-chloro-propane in 10 ml of dimethylsulfoxide, while cooling with ice water. After one hour the mixture was poured into water. After a short time the viscous precipitate began to crystallize. The precipitate was suction-filtered off, dissolved in acetone, precipitated again with water, and then suction-filtered off and dried

Workup

  1. customthe suspension thus obtained
  2. customto crystallize
  3. filtrationThe precipitate was suction-filtered off
  4. dissolutiondissolved in acetone
  5. customprecipitated again with water
  6. filtrationsuction-filtered off
  7. customdried

Sources & evidence

ORD record
ord-da3b1656b1a248548ff895ad77a089ed
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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