Benzyl Bromide → 2-methyl-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

HRID 2177572Notes

Reaction equation

HRID 2177572 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.C(Br)C1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[N:10]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 12239330HCID 12239330, compound

Product 1

HCID 648580652-methyl-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-1-phenyl-1H-imidazo[4,5-c]pyridine (1.05 g, 5 mmol) in CH2Cl2 (5 mL) was added benzyl bromide (3.0 mL, 25 mmol). The solution stirred at rt for 4 h after which time it was concentrated to dryness. The residue was dissolved in MeOH (10 mL) and to it 20% Pd(OH)2C (0.24 g) was added. The reaction was stirred under an atmosphere of hydrogen for 3 h at rt. The mixture was filtered and the filtrate was concentrated under reduced pressure to a white solid (0.60 g, 56% over 2 steps).

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in MeOH (10 mL) and to it 20% Pd(OH)2C (0.24 g)
  3. additionwas added
  4. stirringThe reaction was stirred under an atmosphere of hydrogen for 3 h at rt
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure to a white solid (0.60 g, 56% over 2 steps)

Sources & evidence

ORD record
ord-1e13a28bf8ba4d38ab58e50f3075cf9d
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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