2-(Dimethylamino)ethanol → HCID 21106669, compound

HRID 1765068Notes

Reaction equation

HRID 1765068 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].[CH2:7]([O:14][C:15]1[C:16](Br)=[N:17][CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[Na+]>CN(C=O)C>[CH2:7]([O:14][C:15]1[C:16]([O:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[N:17][CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 107780003-(Benzyloxy)-2-bromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 21106669HCID 21106669, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N,N-dimethylaminoethanol (4.16 g, 46.7 mmol) and (3-benzyloxy)-2-bromopyridine (from Step 1; 8.22 g, 31.1 mmol) in dry DMF (50 mL) was sodium tert-butoxide (5.98 g, 62.2 mmol) added in one portion. The reaction mixture was stirred at 80° C. for 1.5 h, the solvent was removed under reduced pressure and the oily residue was taken up between CHCl3/water. The aqueous phase was extracted twice with CHCl3 and the combined organic layers were washed once with brine, dried (MgSO4), and concentrated under reduced pressure. This gave 8.4 g (100%) of the title compound as a light brown oil. Purity 95% (HPLC). HRMS m/z calcd for C16H20N2O2 (M)+ 272.1525. found 272.1537.

Workup

  1. additionadded in one portion
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous phase was extracted twice with CHCl3
  4. washthe combined organic layers were washed once with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f24da75945c94551829c3aa789daf54b
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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