Sodium Hydroxide → 1-(5-Bromopyridin-3-yl)-N-methylmethanamine

HRID 910286Notes

Reaction equation

HRID 910286 reaction equation
Cl.CN.[C:4]([BH3-])#[N:5].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=O)[CH:12]=[N:13][CH:14]=1.[OH-].[Na+]>CO>[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][NH:5][CH3:4])[CH:12]=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 125150731-(5-Bromopyridin-3-yl)-N-methylmethanamineYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.8 g (27 mmol) of methylamine hydrochloride and then 0.4 g (6 mmol) of sodium cyanoborohydride are successively added to a solution of 1 g (5.4 mmol) of 5-bromopyridine-3-carbaldehyde in 20 ml of methanol. The reaction medium is stirred at room temperature for 2 days. The precipitate is filtered off and the filtrate is evaporated to dryness. The residue is taken up in dichloromethane and washed with water. After extraction, the organic phase obtained is washed with aqueous hydrochloric acid solution. The aqueous phase thus obtained is brought to pH 9 with aqueous sodium hydroxide solution and then extracted with dichloromethane. The organic phase thus obtained is dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 9.5/0.5 dichloromethane/methanol mixture. 0.5 g (50%) of (5-bromopyrid-3-ylmethyl)methylamine is obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. customthe filtrate is evaporated to dryness
  3. washwashed with water
  4. extractionAfter extraction
  5. customthe organic phase obtained
  6. washis washed with aqueous hydrochloric acid solution
  7. customThe aqueous phase thus obtained
  8. extractionextracted with dichloromethane
  9. customThe organic phase thus obtained
  10. dry with materialis dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe residue obtained
  14. customis purified by chromatography on a column of silica
  15. washeluted with a 9.5/0.5 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-8ecef8d6b7ad467a8f02c51a53b8d865
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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