Sodium hydride → HCID 22118499, compound

HRID 365280Notes

Reaction equation

HRID 365280 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][CH2:11][CH2:12][NH2:13].[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>CS(C)=O>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)[CH2:10][CH2:11][CH2:12][NH2:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 10606924N-(3-aminopropyl)pyridin-2-amine

Product 1

HCID 22118499HCID 22118499, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a mixture of sodium hydride (5.86 g, 60% dispersion in mineral oil, 0.1415 mol) in dry dimethylsulfoxide (250 ml) was slowly added a solution of N-(pyridin-2-yl)propane-1,3-diamine (20 g, 0.1323 mol) in dry dimethylsulfoxide (50 ml) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred until gas evolution was ceased. A solution of 4-bromobenzylbromide (36.09 g, 0.1415 mol) in dry dimethylsulfoxide (100 ml) was slowly added at room temperature. The reaction mixture was stirred for 48 h at room temperature. The reaction mixture was poured onto ice water (500 ml) and extracted with ethyl acetate (3×250 ml). The combined organic extracts were washed with water (3×150 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue (40.56 g) was washed with n-heptane (30 ml) which afforded 36.77 g of crude N-(4-bromobenzyl)-N-(pyridin-2-yl)propane-1,3-diamine. 20 g crude product was purified by column chromatography on silica gel (900 ml) using dichloremethane/methanol/triethylamine 9:0.5:0.5 as eluent affording 13.75 g (70%) of N-(4-bromobenzyl)-N-(pyridin-2-yl)propane-1,3-diamine as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 48 h at room temperature
  2. additionThe reaction mixture was poured onto ice water (500 ml)
  3. extractionextracted with ethyl acetate (3×250 ml)
  4. washThe combined organic extracts were washed with water (3×150 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. washThe residue (40.56 g) was washed with n-heptane (30 ml) which

Sources & evidence

ORD record
ord-215d73bd16664a87ad2157bdcf1510cf
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

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