Potassium Carbonate → HCID 10223348, compound

HRID 1244995Notes

Reaction equation

HRID 1244995 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[C:16]#N)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28](C=CC=O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].CN(C)[C:48](=O)[CH3:49]>O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:49]=[CH:48][C:16]([C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)=[C:15]2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 21922745HCID 21922745, compoundHCID 533843793-(4-Fluorophenyl)-2-propenal

Product 1

HCID 10223348HCID 10223348, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.25 g (46.51 mmol) of α-(1-benzylpiperidin-4-yl)amino-α-(pyridin-4-yl)acetonitrile [prepared as described in step 12(ii) above] and 6.98 g (46.51 mmol) of 3-(4-fluorophenyl)acrolein were dissolved in 145 ml of N,N-dimethylacetamide, 1.29 g (9.30 mmol) of potassium carbonate were added to the solution, and then this was stirred at room temperature for 5 hours. At the end of this time, water was added to the reaction mixture and then this was extracted with ethyl acetate. The organic extract was washed with water and then concentrated by evaporation under reduced pressure. 150 ml of ethylene glycol were added to the residue thus obtained and the resulting mixture was stirred at 180° C. for 1 hour. After cooling to room temperature, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture which was then extracted with ethyl acetate. The organic extract was washed with water and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 1:3 by volume mixture of hexane and ethyl acetate as the eluant to give 10.31 g (yield 49%) of the title compound as a pale brown powder.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. addition150 ml of ethylene glycol were added to the residue
  6. customthus obtained
  7. stirringthe resulting mixture was stirred at 180° C. for 1 hour
  8. temperatureAfter cooling to room temperature
  9. extractionwas then extracted with ethyl acetate
  10. extractionThe organic extract
  11. washwas washed with water
  12. concentrationconcentrated by evaporation under reduced pressure
  13. customThe residue thus obtained
  14. customwas purified by chromatography on a silica gel column
  15. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-ee9e3feb7a8d429793a83dbf5855012c
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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