3-(Chloromethyl)pyridine → HCID 19803475, compound

HRID 1681993Notes

Reaction equation

HRID 1681993 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+].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Cl)[CH:24]=1>CS(C)=O>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:9]2[C:8](=[O:12])[CH2:7][C:6]3[CH:13]=[C:14]([O:15][CH3:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:11]=[CH:10]2)[CH:24]=1

Participants

5

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 19803475HCID 19803475, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.2 g (0.01 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one are suspended in 10 ml of dimethyl-sulphoxide and 1.12 g (0.01 mol) of potassium tert.but-oxide are added with stirring. After 60 minutes, 1.3 g (0.01 mol) of 3picolylchloride dissolved in 10 ml of dimethylsulphoxide are added dropwize to the resulting solution with stirring. After 1 hour it is poured onto ice water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over 200 g of aluminium oxide (neutral, activity II-III) with methylene chloride and then with increasing quantities of methanol (up to 0.8%). Yield: 1.4 g (45.2% of theory), Melting point: 144°-146° C.

Workup

  1. additionare added dropwize to the resulting solution
  2. stirringwith stirring
  3. additionAfter 1 hour it is poured onto ice water
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. custompurified over 200 g of aluminium oxide (neutral, activity II-III) with methylene chloride

Sources & evidence

ORD record
ord-411f38cb6de04d2a8a961dd53686e669
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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