Norpyridostigmine → 3-(Dimethylcarbamoyloxy)-1-(cyclopropylcarbonyloxymethyl)pyridinium chloride

HRID 543157Notes

Reaction equation

HRID 543157 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][CH2:14][O:15][C:16]([CH:18]1[CH2:20][CH2:19]1)=[O:17]>>[Cl-:13].[CH3:1][N:2]([CH3:12])[C:3]([O:5][C:6]1[CH:7]=[N+:8]([CH2:14][O:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

3

Reactant 2

HCID 98821NorpyridostigmineHCID 19069329Chloromethyl cyclopropanecarboxylate

Product 1

HCID 202058383-(Dimethylcarbamoyloxy)-1-(cyclopropylcarbonyloxymethyl)pyridinium chlorideYield 92.2%

Procedure

3-Dimethylcarbamoyloxypyridine (1.66 g) and chloromethylcyclopropanecarboxylate (2.70 g) were heated to 90° C. with stirring for 3 hrs. The reaction mixture was treated in a similar manner as described in Example 1 to give 2.77 g of 3-(dimethylcarbamoyloxy)-1-(cyclopropylcarbonyloxymethyl)pyridinium chloride as oil. The structure was determined by N.M.R.

Workup

  1. additionThe reaction mixture was treated in a similar manner

Sources & evidence

ORD record
ord-aa35de5c9b1d480d95953ad73d6d28b4
Source dataset
uspto-grants-1987_04
Patent number
US04661502

Reaction notes

Loading…