1-(4-Nitrophenyl)piperazine → HCID 18403833, compound

HRID 1017685Notes

Reaction equation

HRID 1017685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH:6]=O.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:28]2[CH2:29][CH2:30][N:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)[CH2:26][CH2:27]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 804471-(4-Nitrophenyl)piperazineHCID 4064704HCID 4064704, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18403833HCID 18403833, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-methoxy-4-(methylaminocarbonyloxy)benzaldehyde (1.01 g) in 1,2-dichloroethane (19.0 ml) was added 1-(4-nitrophenyl)piperazine (1.0 g), and sodium triacetoxyborohydride (1.54 g), with stirring. The reaction mixture was stirred for 3 hrs at ambient temperature, poured into ice/saturated sodium carbonate solution (100 ml) and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (silica gel), eluting with dichloromethane, followed by 1% methanol:dichloromethane. The appropriate fractions were collected and concentrated to give 1.66 g (86%) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 155-157° C.

Workup

  1. stirringThe reaction mixture was stirred for 3 hrs at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (silica gel)
  8. washeluting with dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-426a0a58db0645b7aeb460946f838425
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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