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

HRID 543158

Reaction equation

HRID 543158 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](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[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](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

3

Reactant 2

HCID 98821NorpyridostigmineHCID 525229Chloromethyl hexanoate

Product 1

HCID 202058363-(Dimethylcarbamoyloxy)-1-(hexanoyloxymethyl)-pyridinium chlorideYield 80.2%

Procedure

3-Dimethylcarbamoyloxypyridine (1.66 g) and chloromethylhexanoate (2.0 g) were heated to 90° C. with stirring for 3 hours. The reaction mixture was treated in a similar manner as described in Example 1 to give 2.65 g of 3-(dimethylcarbamoyloxy)-1-(hexanoyloxymethyl)-pyridinium chloride as colorless powdery crystals. It was impossible to precisely measure the melting point because of high hygroscopicity. The structure was determined by N.M.R.

Workup

  1. additionThe reaction mixture was treated in a similar manner

Sources & evidence

ORD record
ord-390da6494e7b419eac2dc5ef8c661421
Source dataset
uspto-grants-1987_04
Patent number
US04661502

Linked notes

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