N-[2-(4-Nitro-phenyl)-ethyl]-N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-propionamide → 4-(2-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-propyl-amino}-ethyl)-phenylamine

HRID 1516787Notes

Reaction equation

HRID 1516787 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[C:13](=O)[CH2:14][CH3:15])=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[C:25]1([N:22]2[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][N:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[CH2:20][CH2:21]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 22261339N-[2-(4-Nitro-phenyl)-ethyl]-N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-propionamide

Product 1

HCID 222613434-(2-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-propyl-amino}-ethyl)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-(4-nitro-phenyl)-ethyl]-N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-propionamide 28a (0.33 g, 0.80 mmol) was dissolved in dry EtOH (20 mL) and 10 wt % Pd/C (0.05 g) was added. The mixture was stirred for overnight under H2 at 1 atm. Pressure. The reaction mixture was filtered through celite and filtrate was concentrated under reduced pressure and kept under vacuum for 1 h to give the corresponding aniline. In to the solution of the crude product in 15 ml dry THF was added 1(M) BH3/THF (7 mL, 7 mmol). The reaction mixture was refluxed for 6 h. After the solution was cooled to room temperature, methanol (5 mL) was added slowly. The solvent was removed under reduced pressure and 10% HCl/MeOH (25 mL) was added into the residue and the solution was refluxed for 1 h. Solid NaHCO3 was added and the methanol was removed in vacuo. The mixture was extracted with EtOAc. The combined organic phase was dried over Na2SO4 and evaporated to give the crude product which was purified by chromatography (EtOAc/MeOH=9/1) to give 29a as a colorless oil: 0.23 g (78% yield). 1H NMR (CDCl3, 300 MHz): δ 0.89 (3H, t, J=7.2 Hz, CH3), 1.50 (2H, q, J=7.2 Hz, CH2), 2.48-2.57 (4H, m, CH2Ar, (CH2)N), 2.63-2.75 (10H, m, (CH2)3N, (CH2)2N), 3.20 (4H, t, J=4.8 Hz, (CH2)2NPh), 3.56 (2H, bs, NH2), 6.62 (2H, d, J=8.7 Hz, ArH), 6.85 (1H, t, J=9.6 Hz, ArH), 6.91-6.99 (4H, m, ArH), 7.25 (2H, t, J=9 Hz, ArH). Free base was converted into its hydrochloride salt, mp 262-264° C. Elemental analysis calculated for C23H38N4Cl4,1.05H2O:C, 51.99; H, 7.60; N, 10.54. Found C, 52.37; H, 7.89; N, 10.12.

Workup

  1. filtrationThe reaction mixture was filtered through celite and filtrate
  2. concentrationwas concentrated under reduced pressure
  3. waitkept under vacuum for 1 h

Sources & evidence

ORD record
ord-231829afd55b48219eb1fc8a02c8df34
Source dataset
uspto-grants-2012_07
Patent number
US08227604B2

Reaction notes

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