2-(Dimethylamino)ethanol → HCID 21106684, compound

HRID 1765084Notes

Reaction equation

HRID 1765084 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].CC(C)([O-])C.[K+].CS(O[CH2:18][C:19]1[C:24]([O:25][CH2:26][CH2:27][O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)=[CH:23][CH:22]=[CH:21][N:20]=1)(=O)=O>O1CCOCC1>[O:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH:29]1[O:28][CH2:27][CH2:26][O:25][C:24]1[C:19]([CH2:18][O:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 21106674HCID 21106674, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21106684HCID 21106684, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2-(N,N-dimethylamino)ethanol (0.84 g, 9.4 mmol) in dry dioxane (30 mL) was added potassium tert-butoxide (0.92 g, 8.2 mmol) and the mixture was stirred at room temperature for 20 minutes after which time a solution of {3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}methyl methanesulfonate (from Step 2; 2.1 g, 6.3 mmol) in dioxane (10 mL) was added. The initially slightly exothermic reaction was stirred at ambient temperature overnight. The solvent from the reaction mixture was evaporated under reduced pressure and the resulting oil was taken up between CHCl3/water. The aqueous phase was extracted once with CHCl3 and the combined organic phases were dried (MgSO4) and the solvent was again evaporated. The resulting oil was chromatographed on a column of silica (100 mm, i.d.=30 mm) with initially CHCl3 100% (100 mL) followed by CHCl3/MeOH/NH4OH (95:5:0.2; 100 mL, and thereafter 90:10:0.2) to give 0.74 g (36%) of the title compound as a brown oil. HRMS m/z calcd for C17H28N2O4 (M)+ 324.2049. found 324.2042.

Workup

  1. additionwas added
  2. customThe initially slightly exothermic reaction
  3. customThe solvent from the reaction mixture was evaporated under reduced pressure
  4. extractionThe aqueous phase was extracted once with CHCl3
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. customthe solvent was again evaporated
  7. customThe resulting oil was chromatographed on a column of silica (100 mm, i.d.=30 mm) with initially CHCl3 100% (100 mL)

Sources & evidence

ORD record
ord-8b01e5f7c0ee4632bb6e8be3f1a70dc8
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

Loading…