Toluene → Tert-butyl 4-(3-(4-amino-3-(trifluoromethyl)phenoxy) propyl)piperazine-1-carboxylate

HRID 415077Notes

Reaction equation

HRID 415077 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:6][C:5]=1[C:27]([F:30])([F:29])[F:28])([O-])=O.C([O-])=O.[NH4+].C1(C)C=CC=CC=1>[Fe].O>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:14][CH2:13]2)=[CH:6][C:5]=1[C:27]([F:29])([F:30])[F:28]

Participants

6

Reactant 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 59349553Tert-butyl 4-(3-(4-nitro-3-(trifluoromethyl)phenoxy)propyl)piperazine-1-carboxylate

Product 1

HCID 59349411Tert-butyl 4-(3-(4-amino-3-(trifluoromethyl)phenoxy) propyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A flask was charged with tert-butyl 4-(3-(4-nitro-3-(trifluoromethyl)phenoxy)propyl)piperazine-1-carboxylate (0.78 g, 1.8 mmol), ammonium formate (0.45 g, 7.2 mmol), and iron powder (0.40 g, 7.2 mmol). Toluene (15 mL) and water (15 mL) were added to the flask and the mixture was heated to reflux for 2 hours, after which time, the hot mixture was filtered through a plug of Celite. The solvent was removed on a rotary evaporator under reduced pressure to yield tert-butyl 4-(3-(4-amino-3-(trifluoromethyl)phenoxy) propyl)piperazine-1-carboxylate. The material was used without further purification. MS (EI): 404 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationafter which time, the hot mixture was filtered through a plug of Celite
  4. customThe solvent was removed on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-23d8633550924736af59b4ac62b46501
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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