2-(Dimethylamino)ethanol → HCID 46233349, compound

HRID 1964807Notes

Reaction equation

HRID 1964807 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>CCOCC>[Br:9][C:10]1[N:11]=[C:12]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

Product 1

HCID 46233349HCID 46233349, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

2-dimethylaminoethanol (2 mL, 20 mmol) was added at rt to a suspension of NaH (oil was not removed) in dry DMF (3 mL). The mixture was stirred at rt for 2 hours and 1 h at 60° C. Then commercial 2,6-dibromopyridine (6.16 g, 26 mmol, 1.3 eq) was added at rt and the whole was stirred at rt overnight. The crude mixture was dissolved in some Et2O and was extracted with 2 portions of citric acid 30%. Combined aqueous phases were washed with 2 portions of Et2O. The aqueous phase was basified with NaOH 5N at 0° C. and was extracted with 3 portions of Et2O. Combined organic phases was dried over MgSO4, filtrated and evaporated. As some DMF remained, HCl in Et2O was added. The solvents were evaporated and the resulting solid was put at the pump for 4 hours. It was dissolved in H2O and basified with NaOH 5 M. The desired product (the base) was extracted with 3 portions of Et2O. Combined organic layers were dried over MgSO4, filtrated and evaporated to give the desired product (XXIII), N-{2-[(6-bromo-2-pyridinyl)oxy]ethyl}-N,N-dimethylamine (4.4309 g, 18.076 mmol, 90.4%).

Workup

  1. customwas not removed) in dry DMF (3 mL)
  2. stirringthe whole was stirred at rt overnight
  3. extractionwas extracted with 2 portions of citric acid 30%
  4. washCombined aqueous phases were washed with 2 portions of Et2O
  5. customwas basified with NaOH 5N at 0° C.
  6. extractionwas extracted with 3 portions of Et2O
  7. dry with materialCombined organic phases was dried over MgSO4
  8. filtrationfiltrated
  9. customevaporated
  10. additionHCl in Et2O was added
  11. customThe solvents were evaporated
  12. waitthe resulting solid was put at the pump for 4 hours
  13. dissolutionIt was dissolved in H2O and basified with NaOH 5 M
  14. extractionThe desired product (the base) was extracted with 3 portions of Et2O
  15. dry with materialCombined organic layers were dried over MgSO4
  16. filtrationfiltrated
  17. customevaporated

Sources & evidence

ORD record
ord-8488aa3c686d452f9d3e90a22ec8ea88
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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