Dimethylformamide → 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5methoxy-pyridine-N-oxide

HRID 617363Notes

Reaction equation

HRID 617363 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[N+:11]([O-:16])[CH:12]=[C:13](Br)[CH:14]=1.[C-]#N.[Na+].CN([CH:23]=[O:24])C>O>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[N+:11]([O-:16])[CH:12]=[C:13]([O:24][CH3:23])[CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 213096723-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine 1-oxide

Product 1

HCID 213096733-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5methoxy-pyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-5bromo-pyridine-N-oxide, from Example 98a above, is reacted with sodium cyanide in DMF and water according to standard procedures. The solvents are removed, and the product is extracted, then purified by chromatography on silica gel.

Workup

  1. customThe solvents are removed
  2. extractionthe product is extracted
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-89998bd42b784f44b6e4bbf02bf3ce1e
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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