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

HRID 53236Notes

Reaction equation

HRID 53236 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. 1H NMR CDCl3 δ 7.40-7.25 (m, 5H), 7.22 (d,=8.5 Hz, 2H), 6.90 (d,=8.5 Hz, 2H), 3.45 (m, 2H), 3.00 (m, 1H), 2.80-2.50 (m, 3H), 2.20-1.90 (m, 4H), 2.00 (s, 3H), 1.60-1.50 (m, 2H), 1.30-1.10 (m, 1H).

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-84ad44efd7884afb8db969b02dad5d99
Source dataset
uspto-grants-1997_04
Patent number
US05618830

Reaction notes

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