4-(diphenylmethyl) N-(2-nitrophenyl)-1-piperazinepropanamine hydrochloride → N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine hydrochloride

HRID 1413488Notes

Reaction equation

HRID 1413488 reaction equation
[ClH:1].[C:2]1([CH:8]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-])=O)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Ni].CO>[ClH:1].[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:11][CH2:10][N:9]([CH:8]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 205063614-(diphenylmethyl) N-(2-nitrophenyl)-1-piperazinepropanamine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 20506359N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15 parts of 4-(diphenylmethyl)-N-(2-nitrophenyl)-1-piperazinepropanamine hydrochloride in 160 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over hyflo and the filtrate is evaporated. The solid residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product is filtered off and dried, yielding N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine hydrochloride; mp. 223.1° C.

Workup

  1. filtrationthe catalyst is filtered off over hyflo
  2. customthe filtrate is evaporated
  3. customThe solid residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-c9dc766474f048f0b7031d5982b3c389
Source dataset
uspto-grants-1981_02
Patent number
US04250176

Reaction notes

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