Ammonium Chloride → HCID 66652008, compound

HRID 1751140Notes

Reaction equation

HRID 1751140 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][CH:37]=1)[CH2:7][N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[N:10]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9]1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][CH:37]=1)[CH2:7][N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[N:10]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58046747Benzyl 3-(3-nitrobenzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652008HCID 66652008, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a refluxing solution of benzyl 3-(3-nitrobenzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.77 g, 1.53 mmol) and ammonium chloride (0.96 g, 18.0 mmol) in 2:1 mixture of ethanol/water (18 mL), was added iron powder (0.3 g, 5.4 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 benzyl 3-(3-aminobenzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.80 g, 95%).

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-5e4c23b257d040c585fe355df9884a07
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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