Hydrochloric Acid → HCID 22725156, compound

HRID 2085428Notes

Reaction equation

HRID 2085428 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>C1COCC1>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22725172HCID 22725172, compound

Product 1

HCID 22725156HCID 22725156, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of BH3 in THF (1.0 M, 83.0 mL, 83.0 mmol, 3.5 eq) was added to a stirring solution of 3-(4-phenylpiperidin-1-yl)propionitrile (5.10 g, 24.0 mmol) in anhydrous THF (20 mL) under argon at room temperature. The mixture was heated at reflux temperature for 4.5 hours and then cooled to room temperature. Aqueous 6 N HCl (130 mL) was added and stirring was continued for 2 hours at 50-70° C. The mixture was basified to pH 9 by addition of aqueous 6 N NaOH and extracted with EtOAc (100 mL) and CH2Cl2 (3×100 mL). The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was dissolved in CH2Cl2 (20 mL) and treated with HCl in ether (1.0 M, 50 mL). The solvents were removed, ether (250 mL) was added, the mixture was filtered, and the filter cake was washed with ether. Water (60 mL) was added to the resulting white solid, 1 N NaOH was added until pH 10-11 was reached, and then the aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined extracts were dried over magnesium sulfate and the solvents were evaporated, giving the desired product (4.50 g, 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4.5 hours
  3. extractionextracted with EtOAc (100 mL) and CH2Cl2 (3×100 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  7. additiontreated with HCl in ether (1.0 M, 50 mL)
  8. customThe solvents were removed
  9. additionether (250 mL) was added
  10. filtrationthe mixture was filtered
  11. washthe filter cake was washed with ether
  12. additionWater (60 mL) was added to the resulting white solid, 1 N NaOH
  13. additionwas added until pH 10-11
  14. extractionthe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  15. dry with materialThe combined extracts were dried over magnesium sulfate
  16. customthe solvents were evaporated

Sources & evidence

ORD record
ord-08be6a7d6e804e39bd6980d0bec66aa8
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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