Water → HCID 58181306, compound

HRID 1465504Notes

Reaction equation

HRID 1465504 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]3)=[CH:18][N:17]=2)=[CH:10][CH:9]=1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C)C=O>[C:28]([N:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:18]=[N:17][C:16]([CH2:15][CH2:14][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][N:31]=[N+:32]=[N-:33])=[CH:13][CH:12]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 58181280HCID 58181280, compound

Product 1

HCID 58181306HCID 58181306, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)ethyl methanesulfonate (608.9 mg, 1.411 mmol) in anhydrous N,N-dimethylformamide (5 ml) was added sodium azide (918.0 mg, 14.12 mmol), and the mixture was stirred at room temperature for 24 hrs. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with tert-butyl methyl ether (10 ml) and dried under reduced pressure to give 1-acetyl-4-(6-{2-[4-(2-azidoethyl)phenyl]ethyl}pyridin-3-yl)piperazine (405.9 mg, yield 76.0%) as a white solid.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with tert-butyl methyl ether (10 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-86c592756295476281d733ed917112c4
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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