Pyridine → HCID 67030046, compound

HRID 1465456Notes

Reaction equation

HRID 1465456 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClCCl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][NH:13][C:22](=[O:24])[CH3:23])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67030367HCID 67030367, compound

Product 1

HCID 67030046HCID 67030046, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N-(4-bromophenyl)-N-ethylethane-1,2-diamine dihydrochloride (1.044 g, corresponding to 2.33 mmol), pyridine (4 ml) and anhydrous dichloromethane (8 ml) was added dropwise acetic anhydride (0.28 ml, 2.92 mmol) at 0° C. After stirring at room temperature for 70 mins, the reaction mixture was diluted with dichloromethane (50 ml), washed twice with diluted aqueous sodium hydrogen carbonate solution and with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→1:0) to give N-{2-[(4-bromophenyl)(ethyl)amino]ethyl}acetamide (460 mg, overall yield of 2 steps 92%) as a white solid.

Workup

  1. washwashed twice with diluted aqueous sodium hydrogen carbonate solution and with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→1:0)

Sources & evidence

ORD record
ord-0279054c1e5f48e0b6595d05c3cb27d5
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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