Benzhydrylpiperazine → HCID 20298863, compound

HRID 1389296Notes

Reaction equation

HRID 1389296 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:23]2[CH2:24][CH2:25][N:20]([CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:21][CH2:22]2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 70048BenzhydrylpiperazineHCID 936621-Chloro-4-(chloromethyl)-2-nitrobenzene

Product 1

HCID 20298863HCID 20298863, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.3 parts of 1-chloro-4-(chloromethyl)-2-nitrobenzene, 25.2 parts of 1-(diphenylmethyl)piperazine and 120 parts of ethanol is stirred and refluxed for 4 hours. The reaction mixture is cooled and evaporated. The residue is taken up in about 100 parts of water and the products is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and hexane (1:2 by volume). The product is filtered off, washed with hexane and dried, yielding 19.6 parts of 1-(4-chloro-3-nitrophenylmethyl)-4-(diphenylmethyl)piperazine; mp. 101.6° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. extractionthe products is extracted with methylbenzene
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and hexane (1:2 by volume)
  13. filtrationThe product is filtered off
  14. washwashed with hexane
  15. customdried

Sources & evidence

ORD record
ord-0347bec2a63e4d738d2f55ede96071e7
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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