Ammonium Chloride → HCID 66652392, compound

HRID 2363075Notes

Reaction equation

HRID 2363075 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[N:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[N:12]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66652328HCID 66652328, compound

Product 1

HCID 66652392HCID 66652392, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a refluxing solution of tert-butyl 3-(4-nitrophenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.0 g, 2.2 mmol) and ammonium chloride (1.18 g, 22.0 mmol) in 2:1 mixture of ethanol/water (21 mL), was added iron powder (0.37 g, 6.6 mmol) over a period of 45 minutes. After refluxing for another hour, the reaction mixture was extracted with dichloromethane, washed the organic extracts with water and brine. The organic phase was dried over MgSO4 and concentrated to obtain tert-butyl 3-(4-aminophenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.9 g, 97%).

Workup

  1. temperatureAfter refluxing for another hour
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washwashed the organic extracts with water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5cb0f45d1484e11acc0b3226c0942f2
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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