Hydrochloric Acid → HCID 2235157, compound

HRID 382697Notes

Reaction equation

HRID 382697 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCOCC>C1COCC1>[NH2:17][CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 23004105HCID 23004105, compound

Product 1

HCID 2235157HCID 2235157, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(4-benzylpiperidin-1-yl)propionitrile (8.20 g, 35.9 mmol, 1.0 equiv) in anhydrous THF (20 mL) under argon was added a solution of BH3 in THF (1.0 M, 126 mL, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours, then cooled to room temperature and concentrated to a volume of about 30 mL. Aqueous HCl (6 N, 80 mL) was added and stirring was continued for 2 hours at 55-60° C. The mixture was basified to pH 9 by addition of 6 N aq. NaOH and extracted with CH2Cl2 (3×150 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was dissolved in CH2Cl2 (20 mL) and treated with HCl in ether (1.0 M, 75 mL, 2.1 equiv). The solvents were removed, ether (60 mL) was added, the mixture was filtered, and the filter cake was washed with ether (2×30 mL). Water (40 mL) was added to the resulting white solid, the pH was adjusted to 10 with 1 M NaOH, and the aqueous phase was extracted with CH2Cl2 (3×80 mL). The combined organic solutions were dried over MgSO4 and concentrated to give 7.59 g (91%) of colorless oil, which was characterized spectroscopically.

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. concentrationconcentrated to a volume of about 30 mL
  3. additionAqueous HCl (6 N, 80 mL) was added
  4. additionThe mixture was basified to pH 9 by addition of 6 N aq. NaOH
  5. extractionextracted with CH2Cl2 (3×150 mL)
  6. dry with materialThe combined organic solutions were dried over MgSO4
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  9. customThe solvents were removed
  10. additionether (60 mL) was added
  11. filtrationthe mixture was filtered
  12. washthe filter cake was washed with ether (2×30 mL)
  13. additionWater (40 mL) was added to the resulting white solid
  14. extractionthe aqueous phase was extracted with CH2Cl2 (3×80 mL)
  15. dry with materialThe combined organic solutions were dried over MgSO4
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-eb83cc5ffad844689c2a2fefc576cc9e
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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