Ammonium Chloride → HCID 66648666, compound

HRID 418006Notes

Reaction equation

HRID 418006 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH:3]1[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[N+:18]([O-])=O.[Cl-].[NH4+]>CO.[Zn]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH:3]1[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[NH2:18]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 666489551,4-Dimethyl-2-[(4-methyl-2-nitrophenoxy)methyl]piperazine

Product 1

HCID 66648666HCID 66648666, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

1,4-Dimethyl-2-(4-methyl-2-nitro-phenoxymethyl)-piperazine (1.02 g, 3.65 mmol) was dissolved in MeOH (75 mL) and treated with sat'd aqueous ammonium chloride solution until the mixture became turbid. Zinc (0.24 g, 3.65 mmol) was added. The resulting warm reaction mixture was allowed to stir for an additional 30 min at which time LCMS indicate that starting material had been consumed. The reaction was diluted with EtOAc and aqueous Na2CO3 and the layers were separated. The organic layer was washed with saturated NaCl solution and dried over solid anhydrous Na2SO4. The mixture was filtered and concentrated in vacuo to afford the desired aniline.

Workup

  1. temperatureThe resulting warm
  2. customreaction mixture
  3. customhad been consumed
  4. additionThe reaction was diluted with EtOAc and aqueous Na2CO3
  5. customthe layers were separated
  6. washThe organic layer was washed with saturated NaCl solution
  7. dry with materialdried over solid anhydrous Na2SO4
  8. filtrationThe mixture was filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-117403038fcb421b94a560cff5bf9d30
Source dataset
uspto-grants-2012_01
Patent number
US08093244B2

Reaction notes

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