Diethyl Ether → 3-(Dimethylcarbamoyloxy)-1-(pivalyloxymethyl)pyridinium chloride

HRID 543159Notes

Reaction equation

HRID 543159 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]([O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:4].[Cl:13]C[CH2:15][C:16]([CH3:21])([CH3:20])[C:17]([O-:19])=[O:18].[CH2:22](OCC)C>>[Cl-:13].[CH3:1][N:2]([CH3:12])[C:3]([O:5][C:6]1[CH:7]=[N+:8]([CH2:22][O:19][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 98821NorpyridostigmineHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 138819523-(Dimethylcarbamoyloxy)-1-(pivalyloxymethyl)pyridinium chloride

Procedure

3-Dimethylcarbamoyloxypyridine (1.66 g) and chloromethylpivalate (2.26 g) were heated to 90° C. with stirring for 2 hrs. The reaction mixture was cooled to room temperature. To this solution was added anhydrous diethylether to crystallize. The crystals were filtered off, washed three times with anhydrous diethyl ether (50 ml×3) and dried under reduced pressure. Recrystallization from acetone-ether (1:2) gave 2.76 g of 3-(dimethylcarbamoyloxy)-1-(pivalyloxymethyl)pyridinium chloride as colorless powdery crystals, m.p. 154°-155° C.

Workup

  1. customto crystallize
  2. filtrationThe crystals were filtered off
  3. washwashed three times with anhydrous diethyl ether (50 ml×3)
  4. customdried under reduced pressure
  5. customRecrystallization from acetone-ether (1:2)

Sources & evidence

ORD record
ord-ecf438081d774cc982c791719440a59e
Source dataset
uspto-grants-1987_04
Patent number
US04661502

Reaction notes

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