Formaldehyde → HCID 22667251, compound

HRID 277712Notes

Reaction equation

HRID 277712 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH:6]=1.[CH2:13]=O.[CH2:15]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C>[CH3:13][C:6]1[NH:5][C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:3][C:2]=1[CH2:1][N:25]1[CH2:26][CH2:27][CH:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 317384-BenzylpiperidineHCID 178430841HCID 178430841, compound

Product 1

HCID 22667251HCID 22667251, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1 g of 1 methyl-2-phenylimidazole in 10 mL acetic acid were added 0.4 mL of 37% aqueous formaldehyde and 1.2 mL of 4-benzylpiperidine. The reaction mixture was heated at 100° C. for 10 hours and the acetic acid then removed by evaporated under reduced pressure. The residue was dissolved in water and made alkaline with 5% sodium hydroxide and extracted with 2×100 mL of dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and concentrated to small volume under reduced pressure to give 1 methyl-2-phenyl-4-[(4-benzylpiperidin-1-yl)methyl]-imidazole.

Workup

  1. customthe acetic acid then removed
  2. customby evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with 2×100 mL of dichloromethane
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated to small volume under reduced pressure

Sources & evidence

ORD record
ord-9df4b0524a0b46f8bdb9d7e35a2a338c
Source dataset
uspto-grants-2002_03
Patent number
US06358955B1

Reaction notes

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