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

HRID 1384684Notes

Reaction equation

HRID 1384684 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. 1H NMR Spectrum (DMSOd6) 3.00(s, 6H); 4.40(d, 2H); 5.20(t, 1H); 6.45(d, 1H); 6.55(s, 1H); 7.96(d, 1H) MS-ESI: 153 [MH]+

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-5ade582895894658a40c65b28e34c703
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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