Hydrochloric Acid → 1-(3-Aminopropyl)-4,4-dicyclohexylpiperidine

HRID 396640Notes

Reaction equation

HRID 396640 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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.[H][H].Cl.CCOCC.[OH-].[Na+]>CCO.O.[Pd]>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 230041131-(3-Aminopropyl)-4,4-dicyclohexylpiperidineYield 61%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(4,4-diphenylpiperidin-1-yl)propionitrile (1.01 g, 3.48 mmol, 1.00 equiv) in denatured EtOH (50 mL, 5% isopropanol) was stirred at 120-130° C. in the presence of 10% Pd on activated carbon (1.00 g, Aldrich) and hydrogen at 440 psi for 15 hours. The catalyst was filtered out by use of Celite and washed with CH2Cl2 (100 mL) and MeOH (150 mL). After removal of the solvents, the residue was dissolved in CH2Cl2 (10 mL) and treated with HCl in ether (1.0 M, 8.7 mmol, 2.5 equiv). The solvents were removed again and the residue was recrystallized from hot EtOH-ether (1:2). The white solid obtained from filtration of this mixture was taken up in water (40 mL), which was basified to pH 10 by addition of 1 N NaOH and extracted with CH2Cl2 (3×75 mL). The combined organic solutions were dried over MgSO4 and concentrated to afford 650 mg of colorless oil (61%), which was characterized spectroscopically.

Workup

  1. filtrationThe catalyst was filtered out by use of Celite
  2. washwashed with CH2Cl2 (100 mL) and MeOH (150 mL)
  3. customAfter removal of the solvents
  4. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  5. customThe solvents were removed again
  6. customthe residue was recrystallized from hot EtOH-ether (1:2)
  7. customThe white solid obtained from filtration of this mixture
  8. extractionextracted with CH2Cl2 (3×75 mL)
  9. dry with materialThe combined organic solutions were dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b648fbdf059b435fb06524f8a38eeb2f
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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