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

HRID 1380857Notes

Reaction equation

HRID 1380857 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

First, 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one (131.5 g, 0.6 mol) is suspended in dimethylsulphoxide (900 ml) and potassium tert. butoxide (80.8 g, 0.72 mol) is added with stirring. After 10 minutes the resulting solution is added dropwise, while cooling with ice water, to 1-bromo-3-chloropropane (77 ml, 0.72 mol) in dimethylsulphoxide (300 ml).

Workup

  1. additionAfter 10 minutes the resulting solution is added dropwise

Sources & evidence

ORD record
ord-19bc8fd80e58489fb8ecb0f04c8dab32
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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