Benzyl Bromide → N-Benzyl-N-[3-(1H-imidazol-1-yl)propyl]benzamide

HRID 1589187Notes

Reaction equation

HRID 1589187 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([N:9]([CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3584880N-[3-(1H-imidazol-1-yl)propyl]benzamide

Product 1

HCID 20248337N-Benzyl-N-[3-(1H-imidazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.58 g. of N-[3-(1H-imidazol-1-yl)propyl]benzamide, 40 ml. of dimethylformamide, and 0.96 g. of 50% sodium hydride in oil was stirred for 2 hours and 2.62 g. of benzyl bromide was added. The mixture was stirred for 24 hours, concentrated to remove the dimethyl formamide, diluted with water and methylene chloride, and the layers separated. The organic layer was washed with water, dried over magnesium sulfate, and concentrated. The oil was twice washed with hexane and again concentrated. The desired product was obtained as an oil.

Workup

  1. additionA mixture of 4.58 g
  2. concentrationconcentrated
  3. customto remove the dimethyl formamide
  4. additiondiluted with water and methylene chloride
  5. customthe layers separated
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washThe oil was twice washed with hexane
  10. concentrationagain concentrated

Sources & evidence

ORD record
ord-305cdc4c88134a4bb37b46b9121669d9
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

Loading…