Potassium Carbonate → 2-(Chloromethyl)quinoline

HRID 1016372Notes

Reaction equation

HRID 1016372 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-a799972dce8b464d94960a3074693953
Source dataset
uspto-grants-2002_11
Patent number
US06476018B1

Reaction notes

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