Sodium ethoxide → HCID 178466105, compound

HRID 1373677Notes

Reaction equation

HRID 1373677 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[O-:18][CH2:19][CH3:20].[Na+]>C(O)C>[CH2:19]([O:18][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=2)=[CH:4][CH:3]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxide2×HCID 178510961HCID 178510961, compound

Product 1

HCID 178466105HCID 178466105, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-[4-(6-chloro-3-pyridyl)imidazolyl]butylamine (825 mg, 3.3 mmoles) in ethanol (15 ml) was added sodium ethoxide (2.24 g, 33 mmoles). The reaction mixture was heated in a sealed vessel in a 130° C. oil bath for 48 hours; upon cooling more sodium ethoxide was added (1.0 g) and the closed vessel was heated at 150° C. for 48 hours more. Upon cooling the reaction mixture was concentrated and than was taken up in dichloromethane (200 ml) and was washed with water (50 ml). The aqueous layer was extracted further with dichloromethane (2×200 ml), the combined organics were dried over MgSO4, filtered, and concentrated yielding 4-[4-(6-ethoxy-3-pyridyl)imidazolyl]butylamine (747 mg, 87%). MH+(261).

Workup

  1. additionwas added (1.0 g)
  2. temperaturethe closed vessel was heated at 150° C. for 48 hours more
  3. temperatureUpon cooling the reaction mixture
  4. concentrationwas concentrated
  5. washwas washed with water (50 ml)
  6. extractionThe aqueous layer was extracted further with dichloromethane (2×200 ml)
  7. dry with materialthe combined organics were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2751b30c23374bff83ac3740e0f490e7
Source dataset
uspto-grants-2007_01
Patent number
US07163924B2

Reaction notes

Loading…