4-(Chloromethyl)pyridinium chloride → HCID 70087909, compound

HRID 1459407Notes

Reaction equation

HRID 1459407 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]([NH:7][CH:8]1[CH2:13][CH:12]2[C:14]([CH3:16])([CH3:15])[C:9]1([CH3:17])[CH2:10][CH2:11]2)=[O:6].[CH3:19][O-].[Na+].[N:22]1[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][CH:23]=1.Cl.[N:31]1[CH:36]=[CH:35][C:34](CCl)=[CH:33][CH:32]=1>CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]([C:34]1[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=1)([C:5](=[O:6])[NH:7][CH:8]1[CH2:13][CH:12]2[C:14]([CH3:15])([CH3:16])[C:9]1([CH3:17])[CH2:10][CH2:11]2)[CH:28]([CH3:19])[C:25]1[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 745714-(Chloromethyl)pyridineHCID 10942334Sodium MethoxideHCID 69849849HCID 69849849, compound

Product 1

HCID 70087909HCID 70087909, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-malonamic acid methyl ester (0.95 g, 3.7 mmol) in methanol (7 ml), sodium methoxide (0.20 g, 3.7 mmol) was added, and the mixture was stirred for 1 hour at ambient temperature. 4-Picolylchloride (0.53 g, 4.1 mmol of freshly liberated free base from 4-picolyl chloride hydrochloride; Aldrich Chemical Co.) was added, and the reaction was then stirred for 18 hours at ambient temperature. Ethyl acetate and water (15 ml of each) were added, and the mixture was well shaken. The separated aqueous extracted was then extracted with an equal volume portion of fresh ethyl acetate. The combined organic extracts were dried (anhydrous sodium sulfate), and concentrated in vacuo to an orange oil (1.16 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with initially ethyl acetate and subsequently with methanol/ethyl acetate up to a 1:4 ratio, respectively, in volume) afforded the title compound (12 mg) as an oil.

Workup

  1. addition) was added
  2. stirringthe reaction was then stirred for 18 hours at ambient temperature
  3. stirringthe mixture was well shaken
  4. extractionThe separated aqueous extracted
  5. extractionwas then extracted with an equal volume portion of fresh ethyl acetate
  6. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  7. concentrationconcentrated in vacuo to an orange oil (1.16 g)
  8. washelution with initially ethyl acetate

Sources & evidence

ORD record
ord-36642c6fc8af4b6fa6904e65f8d180f6
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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