Piperidine → HCID 347464, compound

HRID 1712865Notes

Reaction equation

HRID 1712865 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH3:23])([O-:13])=[O:12].N1CCCCC1>C1(C)C(C)=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[CH:23][C:15]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=2[N+:11]([O-:13])=[O:12])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 84612,4-DinitrotolueneHCID 312444-Methoxybenzaldehyde

Product 1

HCID 347464HCID 347464, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a 2 liter 3-necked round-bottomed flask equipped with a condenser, a Dean-Stark trap, a mechanical stirrer, nitrogen inlet, heating mantle, thermometer, and a Therm-o-watch® temperature controller, was added p-anisaldehyde (149.8 grams, 1.1 moles), 2,4-dinitrotoluene (182 grams, 1.0 mole), xylene (500 milliliters), and piperidine (50 milliliters, 0.5 mole). The resulting mixture was heated with the temperature on the Therm-o-watch® temperature controller set at 145° C. After stirring and heating for about 2 hours, approximately 20 milliliters of water had collected in the Dean-Stark trap. The reaction solution was allowed to cool to room temperature, and then further cooled with an ice water bath for an additional hour during which time the desired product crystallized from the solution. The solid material was filtered, rinsed with pentane, and dried in a vacuum oven at 100° C. for 12 hours to give 257.1 grams (85.6 percent of theory) of the desired product as a dark red crystalline solid.

Workup

  1. customTo a 2 liter 3-necked round-bottomed flask equipped with a condenser
  2. temperaturea Dean-Stark trap, a mechanical stirrer, nitrogen inlet, heating mantle
  3. temperatureThe resulting mixture was heated with the temperature on the Therm-o-watch® temperature controller
  4. customset at 145° C
  5. temperatureheating for about 2 hours
  6. customapproximately 20 milliliters of water had collected in the Dean-Stark trap
  7. temperaturefurther cooled with an ice water bath for an additional hour during which time the desired product
  8. customcrystallized from the solution
  9. filtrationThe solid material was filtered
  10. washrinsed with pentane
  11. customdried in a vacuum oven at 100° C. for 12 hours

Sources & evidence

ORD record
ord-5b4198db8ecf449eb2e7516e2df34e5f
Source dataset
uspto-grants-2010_09
Patent number
US07794896B2

Reaction notes

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