Ammonium formate → HCID 54089766, compound

HRID 429842Notes

Reaction equation

HRID 429842 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([N:14]([C@@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH2:15][CH2:16][CH3:17])[CH3:13])=[CH:7][CH:6]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Fe]>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@H:12]([N:14]([C@@H:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19])[CH2:15][CH2:16][CH3:17])[CH3:13])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69143453HCID 69143453, compound

Product 1

HCID 54089766HCID 54089766, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(R,R)-N-[2-(4-Nitrophenyl)-1-methylethyl]-N-propyl-(1-phenylethyl)amine hydrochloride was dissolved in ethanol (100 ml) and water (16 ml). To this solution was added iron powder (2.44 g) and ammonium formate (2.25 g). The mixture was heated at reflux for 3 hours, cooled to room temperature and filtered through a glass fiber filter. The filtrate was evaporated in vacuo, and the residue was partitioned between ethyl acetate and dilute sodium hydroxide. The organic layer was dried over sodium sulfate, filtered, and the solvent removed in vacuo to give (R,R)-N-[2-(4-aminophenyl)-1-methylethyl]-N-propyl-(1-phenylethyl)amine as a yellow syrup (2.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered through a glass fiber
  4. filtrationfilter
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was partitioned between ethyl acetate and dilute sodium hydroxide
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7fc6cc474dcd4f29a83c0a9f7d3dddad
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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