1-Benzyl-4-piperidone → HCID 21918910, compound

HRID 2249443Notes

Reaction equation

HRID 2249443 reaction equation
[H-].[Na+].[CH2:3](P([O-])(=O)[O-])[P:4]([O:9][CH2:10][CH3:11])(=[O:8])[O:5][CH2:6][CH3:7].C([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)C1C=CC=CC=1>O1CCCC1>[NH:23]1[CH2:28][CH2:27][CH:26]([CH2:3][P:4](=[O:8])([O:9][CH2:10][CH3:11])[O:5][CH2:6][CH3:7])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydrideHCID 86591728HCID 86591728, compound

Product 1

HCID 21918910HCID 21918910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.11 g (528 mmol) of 60% strength sodium hydride are initially charged in 50 ml of absolute tetrahydrofuran, and 15.7 g (52.8 mmol) of diethyl methanediphosphonate are added dropwise. The mixture is stirred at room temperature for another 30 minutes, and 10.1 g (52.8 mmol) of 1-benzyl-4-piperidone are then added. The mixture is stirred for one hour at room temperature and for one hour under reflux, concentrated, admixed with water and extracted three times with dichloromethane, and the organic phases are dried over sodium sulphate and concentrated. The residue is hydrogenated in 50 ml of ethanol over 1.7 g of 10% palladium-carbon at room temperature and 3 bar. The catalyst is filtered off with suction and the filtrate is concentrated.

Workup

  1. stirringThe mixture is stirred for one hour at room temperature and for one hour
  2. temperatureunder reflux
  3. concentrationconcentrated
  4. extractionextracted three times with dichloromethane
  5. dry with materialthe organic phases are dried over sodium sulphate
  6. concentrationconcentrated
  7. customis hydrogenated in 50 ml of ethanol over 1.7 g of 10% palladium-carbon at room temperature
  8. filtrationThe catalyst is filtered off with suction
  9. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-6a8ee8ef161d4699b404136c705c524f
Source dataset
uspto-grants-2008_01
Patent number
US07314871B2

Reaction notes

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