Ammonia → 6-(4-Isopropyl-piperazin-1-yl)-pyridin-3-ylaniline

HRID 43068Notes

Reaction equation

HRID 43068 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12]C=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:19][CH2:20]O.O.[NH3:23]>[Fe].CC(O)=O>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:23]=[CH:12][C:13]([NH:16][C:20]3[CH:19]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 669145306-(4-Isopropyl-piperazin-1-yl)-pyridin-3-ylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-isopropyl-4-(4-nitro-phenyl)-piperazine (Step 33.2) (1.58 g, 6.32 mmol), iron (1.4 g, 25.3 mmol, 4 equiv), EtOH (20 mL), H2O (5 mL) and AcOH (2.5 mL) was stirred for 2 h at 90° C. The reaction mixture was allowed to cool to rt, basified by addition of aqueous NH3, filtered through a pad of celite. The filtrate was concentrated (to remove EtOH), extracted with EtOAc and DCM, saturated with NaCl and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1) afforded 1.1 g of the title compound as a purple solid: ESI-MS: 221.1 [M+H]+; TLC: Rf=0.20 (DCM/MeOH/NH3aq, 91:8:1).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. custom(to remove EtOH)
  5. extractionextracted with EtOAc and DCM, saturated with NaCl
  6. extractionextracted with DCM
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification of the residue by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1)

Sources & evidence

ORD record
ord-975933a2a4f64e45a573a2ed46ff01c3
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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