Potassium Carbonate → 2-(Chloromethyl)quinoline

HRID 324301Notes

Reaction equation

HRID 324301 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C([O-])([O-])=O.[K+].[K+]>O>[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 203942-(Chloromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Chloromethyl)quinoline monohydrochloride (4.06 g) was taken up in water, alkalized with K2CO3 and extracted with DCM. The organic layer was dried (MgSO4), filtered and evaporated, yielding 2-(chloromethyl)quinoline. Sodium hydride (0.7 g) was added at room temperature to a solution of intermediate 8 (6.5 g) in DMF (350 ml) and the mixture was stirred for 30 minutes. 2-(Chloromethyl)quinoline dissolved in DMF was added and the mixture was stirred at 50° C. for 3 hours. The mixture was evaporated, the residue was taken up in water and extracted with DCM. The organic layer was dried (MgSO4), filtered and evaporated. The residue was crystallized from ACN, the precipitate was filtered off, yielding 5.52 g (64%) of 11-[1-[[3,5-dimethoxy-4-(2-quinolinylmethoxy)-phenyl]methyl]-4-piperidinylidene]-6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine (compound 32, mp. 214.8° C.).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-782684af417246f9818af1d661f1dcc8
Source dataset
uspto-grants-2001_04
Patent number
US06218381B1

Reaction notes

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