Ammonium Chloride → HCID 53635909, compound

HRID 1267911Notes

Reaction equation

HRID 1267911 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([N+:22]([O-])=O)[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH2:22])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 536734364-(4-Methyl-3-nitro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 53635909HCID 53635909, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To crude 4-(4-methyl-3-nitro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (3.5 g) in EtOH/water (60 ml, 1:1) was added iron powder (4 g) and solid NH4Cl (4 g) and the mixture heated to reflux temperature for 1.5 hr. After cooling to room temperature the reaction was filtered through Celite and the filter cake washed with further EtOH. The majority of the solvent was removed in vacuo before addition of ethyl acetate and aqueous K2CO3. The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated, to leave an oil that was triturated with isohexanes to afford a pale brown solid (3 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux temperature for 1.5 hr
  3. filtrationwas filtered through Celite
  4. washthe filter cake washed with further EtOH
  5. customThe majority of the solvent was removed in vacuo before addition of ethyl acetate and aqueous K2CO3
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customto leave an oil that
  11. customwas triturated with isohexanes

Sources & evidence

ORD record
ord-834f0e3eda3e4930bbac06d6f4b069b9
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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