Sodium hydride → HCID 22118537, compound

HRID 365286Notes

Reaction equation

HRID 365286 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:13][CH2:14][CH2:15][CH2:16][NH2:17].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CS(C)=O>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:13]([C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:3]=2)[CH2:14][CH2:15][CH2:16][NH2:17])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 22118517N~1~-(Quinolin-2-yl)propane-1,3-diamine

Product 1

HCID 22118537HCID 22118537, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a mixture of sodium hydride (2.64 g, 60% dispersion in mineral oil, 63.79 mmol) in dry dimethylsulfoxide (100 ml) was slowly added a solution of N-(quinolin-2-yl)propane-1,3-diamine (12 g, 56.62 mmol) in dry dimethylsulfoxide (25 ml) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred until gas evolution was ceased. To the resulting mixture a solution of 4-bromobenzylbromide (16.27 g, 63.79 mmol) in dry dimethylsulfoxide (50 ml) was slowly added at room temperature. The reaction mixture was stirred for 4 days at room temperature poured on to ice water (800 ml) and extracted with ethyl acetate (5×150 ml). The combined organic extracts were washed with water (4×150 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue (22.27 g) was washed with n-heptane (30 ml) which afforded 20.41 g of crude N-(4-bromobenzyl)-N-(quinolin-2-yl)propane-1,3-diamine which was purified by column chromatography on silica gel (900 ml) using a mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent affording 13.9 g (63%) of N-(4-bromobenzyl)-N-(quinolin-2-yl)propane-1,3-diamine as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 4 days at room temperature
  2. extractionextracted with ethyl acetate (5×150 ml)
  3. washThe combined organic extracts were washed with water (4×150 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. washThe residue (22.27 g) was washed with n-heptane (30 ml) which

Sources & evidence

ORD record
ord-015a1735f71445b0924ed2e389935270
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

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