1-(5-Imidazol-1-yl-2-nitro-phenyl)-piperidine → 4-Imidazol-1-yl-2-piperidin-1-yl-phenylamine

HRID 32891Notes

Reaction equation

HRID 32891 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:18]([O-])=O)=[C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>C1COCC1.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH2:18])=[C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 693102461-(5-Imidazol-1-yl-2-nitro-phenyl)-piperidine

Product 1

HCID 693102344-Imidazol-1-yl-2-piperidin-1-yl-phenylamineYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(5-imidazol-1-yl-2-nitro-phenyl)-piperidine (117 mg, 0.430 mmol, as prepared in the previous step) in 3 mL of THF was added 6.5 mL of 10% TiCl3 in H2O dropwise over 3 min. After 10 min, the reaction was extracted with 20 mL of EtOAc, and the organic layer was discarded. The aqueous layer was basified with 10M NaOH to pH>9, then extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated in vacuo to afford 74 mg (66%) of the title compound as a light brown solid. Mass spectrum (ESI, m/z): Calcd. for C14H18N4, 243.1 (M+H), found 243.2;

Workup

  1. extractionthe reaction was extracted with 20 mL of EtOAc
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5833059e3f8d4fffa51807339b852015
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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