Methanol → HCID 178493108, compound

HRID 2055146Notes

Reaction equation

HRID 2055146 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=1.[CH3:18][O-:19].[Na+].CO>>[CH3:18][O:19][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 178510962HCID 178510962, compound

Product 1

HCID 178493108HCID 178493108, compoundYield 96%

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[4-(4-chloro-3-pyridyl)imidazolyl]butylamine (400 mg, mmoles) was added sodium methoxide, 5.3 M in methanol (10 ml, 53 mmoles). The reaction mixture was heated at 70° C. for 2 hours. Upon cooling the reaction mixture was concentrated to around 4 ml and then was taken up in dichloromethane (125 ml) and was washed with water (20 ml). The aqueous layer was extracted further with dichloromethane (125 ml), the combined organics were dried over MgSO4, filtered, and concentrated yielding 4-[4-(4-methoxy-3-pyridyl)imidazolyl]butylamine (379 mg, 96%). MH+(247)

Workup

  1. temperatureUpon cooling the reaction mixture
  2. concentrationwas concentrated to around 4 ml
  3. washwas washed with water (20 ml)
  4. extractionThe aqueous layer was extracted further with dichloromethane (125 ml)
  5. dry with materialthe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-66d2842ca3204c52bf694ef54cf2a5d4
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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