Sodium Hydroxide → 4-Cyclohexylpiperidine

HRID 322146Notes

Reaction equation

HRID 322146 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 1N 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-55541cb79fa54bc7b1458b552ddd8033
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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