HCID 21106684, compound → HCID 21106654, compound

HRID 1765085Notes

Reaction equation

HRID 1765085 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([CH2:17][O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[N:13][CH:14]=[CH:15][CH:16]=1>CC(O)=O>[CH3:22][N:21]([CH3:23])[CH2:20][CH2:19][O:18][CH2:17][C:12]1[C:11]([O:10][CH2:9][CH2:8][OH:7])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

3

Reactant 1

HCID 21106684HCID 21106684, compound

Product 1

HCID 21106654HCID 21106654, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-{[3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)pyridin-2-yl]methoxy}ethyl)-N,N-dimethylamine (from Step 3; 0.69 g, 2.13 mmol) in 2 M HOAc (20 mL) was stirred at 50° C. for two days. The reaction mixture was washed with CHCl3 (×3), saturated with sodium chloride, made basic by addition of 8 M NaOH, and extracted with CHCl3 (×3). The solvent from the combined organic phases was removed under reduced pressure to give 0.47 g (92%) of the title compound as a light brown oil. HRMS m/z calcd for C12H20N2O3 (M)+ 240.1474. found 240.1476.

Workup

  1. washThe reaction mixture was washed with CHCl3 (×3), saturated with sodium chloride
  2. additionmade basic by addition of 8 M NaOH
  3. extractionextracted with CHCl3 (×3)
  4. customThe solvent from the combined organic phases was removed under reduced pressure

Sources & evidence

ORD record
ord-6b3dd9b6b72048538d25a9324147b9c1
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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