Acetonitrile → HCID 21477689, compound

HRID 2395782Notes

Reaction equation

HRID 2395782 reaction equation
[CH3:1][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].Br[C:22]([CH3:24])=[CH2:23].C(#N)C>ClCCl.C(=O)([O-])[O-].[K+].[K+]>[CH3:3][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:18]([NH:19][CH2:24][CH:22]=[CH2:23])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 112022-BromopropeneHCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 21477689HCID 21477689, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent2×

Procedure

A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication 88/08424, 2.78 g), 2-bromopropene (1.87 g), anhydrous potassium carbonate (3.3 g) and acetonitrile (100 ml) is refluxed for 36 hr. The mixture is cooled and then diluted with dichloromethane and aqueous potassium carbonate solution. The phases are separated and the organic phase is washed with saline and than concentrated in vacuo. Purification by flash column chromatography (2% methanol/chloroform) provided of the title compound. Capillary GC analysis (HP1 column, initial temperature at 100° for 1 min, then programmed to rise 20° per minute to 250°) gave a peak at 6.06 (96%) minutes.

Workup

  1. temperatureis refluxed for 36 hr
  2. temperatureThe mixture is cooled
  3. customThe phases are separated
  4. washthe organic phase is washed with saline
  5. concentrationthan concentrated in vacuo
  6. customPurification by flash column chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-3108745ce2594c7e8bc1483b4b178e65
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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