Dimethylamine → [2-(dimethylamino)-4-pyridinyl]methanol(SALTDATA: HCl)

HRID 279673Notes

Reaction equation

HRID 279673 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][NH:11][CH3:12]>C(O)C>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:11]([CH3:12])[CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 22625066[2-(dimethylamino)-4-pyridinyl]methanol(SALTDATA: HCl)Yield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-4-hydroxymethylpyridine (1.0 g, 7 mmol), (prepared as described for the starting material in Example 58), and dimethylamine (30 ml of a 30% solution in ethanol) was heated in a Carius tube for 16 hours at 200° C. The mixture was allowed to cool and the mixture partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was separated, dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate to give 4-hydroxymethyl-2-(dimethylamino)pyridine (1 g, 94%) as a yellow oil.

Workup

  1. custom(prepared
  2. temperatureto cool
  3. customthe mixture partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe volatiles removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1efc2d88839847949e671cd7816de0e3
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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