N-(4,5-dichloro-2-nitrophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine → 4,5-dichloro-N1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,2-benzenediamine

HRID 354949Notes

Reaction equation

HRID 354949 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[C:4]([N+:32]([O-])=O)[CH:3]=1.[H][H]>[Ni].CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:32])[C:5]([NH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][CH2:18]2)=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 20506343N-(4,5-dichloro-2-nitrophenyl)-4-(diphenylmethyl)-1-piperazinepropanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 537535764,5-dichloro-N1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,2-benzenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8 parts of N-(4,5-dichloro-2-nitrophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine and 200 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated, yielding 4,5-dichloro-N1 -{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1,2-benzenediamine as an oily residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-504c689d2ff846678b07789978575bed
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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