Sodium Carbonate → 889851-56-3

HRID 490083Notes

Reaction equation

HRID 490083 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>O.CN(C=O)C>[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)[CH2:23][CH2:22]1)[CH3:20]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 16748394889851-56-3Yield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g (14 mmol) 6-chloronicotinonitrile (commercially available) and 0.88 g (7 mmol) N,N-diisopropylethylamine in 20 ml water and 4 ml DMF was heated to 80° C. During 2 min 1.98 g (17 mmol) N-ethylpiperazine was added and stirred at 80° C. for 1 h. 100 ml 1M aq. Na2CO3 solution was added and the mixture was extracted three times with 100 ml ethyl acetate each. The combined organic phases were washed twice with 100 ml brine each and dried with MgSO4. After evaporation the residue was purified with flash chromatography on Alox eluting with a gradient of ethyl acetate/heptan to yield 1.4 g (45%) of the title compound as slightly yellow crystals. (m/e): 21702 (MH+; 100%).

Workup

  1. extractionthe mixture was extracted three times with 100 ml ethyl acetate each
  2. washThe combined organic phases were washed twice with 100 ml brine each and
  3. dry with materialdried with MgSO4
  4. customAfter evaporation the residue
  5. customwas purified with flash chromatography on Alox
  6. washeluting with a gradient of ethyl acetate/heptan

Sources & evidence

ORD record
ord-0c4741cb8e974cf58fc30d685734674e
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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