Piperidine → 1,1'-[4-Nitro-1,2-phenylenebis(methylene)]bispiperidine

HRID 1156023Notes

Reaction equation

HRID 1156023 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:12]Br)[C:7]([CH2:10]Br)=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:6]([CH2:12][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 108523601,2-Bis(bromomethyl)-4-nitrobenzene

Product 1

HCID 130417341,1'-[4-Nitro-1,2-phenylenebis(methylene)]bispiperidineYield 59%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 ml. round-bottomed reaction flask equipped with magnetic stirrer, reflux condenser and nitrogen-inlet tube, there were placed 10 g. (0.032 mole) of crude 4-nitro-α,α'-dibromo-o-xylene [M. Kerfanto, Bulletin de la Societe Chimique de France, Vol. 12, p. 3537 (1965)] and 44.8 g. (0.526 mole) of piperidine (52 ml.) all dissolved in 100 ml. of benzene. The resulting mixture was then heated at the reflux point for a period of 18 hours and finally cooled to room temperature (~25° C.). The spent reaction mixture was then diluted with 500 ml. of benzene and thereafter washed with four-100 ml. portions of water, followed by drying over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there was obtained a 59% yield of crude 1,1'-[4-nitro-1,2-phenylenebis(methylene)]bispiperidine as a residue in the form of a yellow oil.

Workup

  1. customround-bottomed reaction flask equipped with magnetic stirrer
  2. temperaturereflux condenser and nitrogen-inlet tube
  3. temperatureThe resulting mixture was then heated at the reflux point for a period of 18 hours
  4. customThe spent reaction mixture
  5. additionwas then diluted with 500 ml
  6. washof benzene and thereafter washed with four-100 ml
  7. dry with materialby drying over anhydrous magnesium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby means of filtration
  10. customthe solvent by means of evaporation under reduced pressure

Sources & evidence

ORD record
ord-4ca167fcf6824189b001b2b8918556d2
Source dataset
uspto-grants-1982_06
Patent number
US04333932

Reaction notes

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