Sodium Hydroxide → 4-Cyclohexylpiperidine

HRID 382699Notes

Reaction equation

HRID 382699 reaction equation
Cl.[CH:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+]>O>[CH:2]1([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 177497814-Cyclohexylpiperidine hydrochloride

Product 1

HCID 4242404-CyclohexylpiperidineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-phenylpyridine hydrochloride (4.50 g, 29.0 mmol, 1.00 equiv) in denatured EtOH (100 mL, 5% isopropanol) was stirred at 110-120° C. in the presence of 10% Pd on activated carbon (4.50 g, Aldrich) and hydrogen at 440 psi for 24 hours. The catalyst was filtered out by use of Celite and washed with CH2Cl2 (100 mL) and MeOH (150 mL). The filtrate was concentrated to give 5.32 g (90%) of white solid, which was characterized spectroscopically as 4-cyclohexylpiperidine hydrochloride. This white solid was taken up in water (150 mL), which was basified to pH 10 by addition of 1 N NaOH and extracted with CH2Cl2 (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated to afford 4.27 g of white solid (88%), which was characterized spectroscopically.

Workup

  1. extractionextracted with CH2Cl2 (3×200 mL)
  2. dry with materialThe combined organic solutions were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f4f32363d2df47778444863b2c5a66d5
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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