Benzyl Chloride → N-Benzyl-3-acetyl-3-(4-chlorobenzyl)-piperidine

HRID 2259928Notes

Reaction equation

HRID 2259928 reaction equation
Cl.[C:2]([C:5]1([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:4])[CH3:3].C(=O)(O)[O-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[CH2:24]([N:7]1[CH2:8][CH2:9][CH2:10][C:5]([C:2](=[O:4])[CH3:3])([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[CH2:6]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 516892Sodium Bicarbonate2×HCID 199621803-Acetyl-3-(4-Chlorobenzyl)-piperidine hydrochloride

Product 1

HCID 19962175N-Benzyl-3-acetyl-3-(4-chlorobenzyl)-piperidineYield 59.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-Acetyl-3-(4-Chlorobenzyl)-piperidine hydrochloride (0.7 g, 2.43 mmol) in acetonitrile (20 mL) was treated with solid sodium bicarbonate (200 mg, 4.8 mmol) and benzyl chloride (369 mg, 2.9 mol) and heated to reflux for 2 hours. The reaction was then cooled to room temperature, poured into saturated aqueous sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 2% methanol/chloroform to give 492 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 2% methanol/chloroform

Sources & evidence

ORD record
ord-dbefbc949db94528a12aa9e4b6be4455
Source dataset
uspto-grants-1995_12
Patent number
US05475109

Reaction notes

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