Benzaldehyde → Methyl 1-[4-(N-benzylamino)-benzyl]-2-butyl-4-chloroimidazole-5-acetate

HRID 847038Notes

Reaction equation

HRID 847038 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:10]([Cl:17])[N:9]=[C:8]2[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH2:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:10]([Cl:17])[N:9]=[C:8]2[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:22][CH:23]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 240Benzaldehyde2×HCID 15356445Methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetate

Product 1

HCID 19815423Methyl 1-[4-(N-benzylamino)-benzyl]-2-butyl-4-chloroimidazole-5-acetateYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetate (1.00 g, 3.0 mmol, 1 eq), benzaldehyde (0.30 mL, 3.0 mmol, 1 eq), 4 Å powdered molecular sieves (enough to make a slurry) and 40 mL THF was stirred overnight. The next day, more benzaldehyde (0.2 mL) and acidic Al2O3 (activity 1, 1 g) were added and the slurry stirred another 24 hours. The solids were filtered and the solvent from the filtrate removed in vacuo. The residue was dissolved in methanol (10 mL) and sodium cyanoborohydride was added (0.19 g, 3.0 mmol, 1 eq). The mixture was stirred for 24 hours, after which the solvent was removed in vacuo to yield a green oil which was flash chromatographed over silica gel in 70:30 hexane/ethyl acetate to give 740 mg of product as an oil. NMR (200 MHz, CDCl3) δ7.42-7.24 (m, 5H); 6.74 (d, 2H, J=7 Hz); 6.56 (d, 2H, J=7 Hz); 4.98 (s, 2H); 4.31 (s, 2H); 3.61 (s, 3H); 3.48 (s, 2H); 2.60 (t, 2H, J=7 Hz); 1.67 (t of t, 2H, J=7,7 Hz); 1.35 (t of q, 2H, J=7,7 Hz); 0.89 (t, 3H, J=7 Hz). Mass Calcd. for C24H28ClN3O2 : 425.1868. Found: 425.1853.

Workup

  1. stirringthe slurry stirred another 24 hours
  2. filtrationThe solids were filtered
  3. customthe solvent from the filtrate removed in vacuo
  4. dissolutionThe residue was dissolved in methanol (10 mL)
  5. additionsodium cyanoborohydride was added (0.19 g, 3.0 mmol, 1 eq)
  6. stirringThe mixture was stirred for 24 hours
  7. customafter which the solvent was removed in vacuo
  8. customto yield a green oil which
  9. customchromatographed over silica gel in 70:30 hexane/ethyl acetate

Sources & evidence

ORD record
ord-666b714ab44f476d83c7a8e58e812944
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

Loading…