Sodium Hydroxide → HCID 19760350, compound

HRID 1586975Notes

Reaction equation

HRID 1586975 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[OH-].[Na+].Cl.[NH2:25]O>C(O)C>[NH2:25][CH:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:20][CH3:21])[CH2:1][CH3:2])=[O:19])=[CH:6][CH:7]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19760349HCID 19760349, compound

Product 1

HCID 19760350HCID 19760350, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-Diethyl-4-[(4-oxo-1-piperidinyl)methyl]benzamide (58.74 g, 193 mmol) is dissolved in 580 mL of ethanol and treated with 290 mL of 30% NaOH followed by hydroxylamine hydrochloride (26.82 g, 386 mmol). The mixture is refluxed for 45 minutes, the heating mantle removed and the reaction mixture stirred with an overhead stirrer as 38.4 g of 50/50 aluminum-nickel alloy (powder) are added in small portions with ice cooling. After the addition, the mixture is refluxed for 1.75 hours, then allowed to stand at room temperature overnight, filtered through Solka Floc and most of the ethanol is evaporated in vacuo from the filtrate. The resulting aqueous phase is extracted with 3×100 mL of ether. The pooled extracts are concentrated in vacuo and the oily residue is poured into 500 mL of brine and continuously extracted with ether overnight. Concentration of the extract affords 37 g of product which is purified by flash chromatography on silica gel (110 mm column, 5% ammonia saturated methanol in methylene chloride eluent) affording 7.08 g (24.4 mmol, 13% yield) of product: 1H NMR (Me2SO-d6, 300 MHz) δ7.33 (d,J=8.2 Hz, 2H), 7.27 (d,J=8.2 Hz, 2H), 1.0-3.5 (m, 21H).

Workup

  1. temperatureThe mixture is refluxed for 45 minutes
  2. customthe heating mantle removed
  3. additionare added in small portions with ice cooling
  4. additionAfter the addition
  5. temperaturethe mixture is refluxed for 1.75 hours
  6. filtrationfiltered through Solka Floc and most of the ethanol
  7. customis evaporated in vacuo from the filtrate
  8. extractionThe resulting aqueous phase is extracted with 3×100 mL of ether
  9. concentrationThe pooled extracts are concentrated in vacuo
  10. additionthe oily residue is poured into 500 mL of brine
  11. extractioncontinuously extracted with ether overnight

Sources & evidence

ORD record
ord-8c6d836bac944312b79907625fd74b04
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

Loading…