HCID 58902472, compound → 2-Amino-1-[2-[4-(tert-butoxycarbonyl)piperazin-1-yl]ethoxy]-4-(trifluoromethyl)benzene

HRID 1640133Notes

Reaction equation

HRID 1640133 reaction equation
[N+:1]([C:4]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)([O-])=O>[Pd].CCOC(C)=O>[NH2:1][C:4]1[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 58902472HCID 58902472, compound

Product 1

HCID 589022452-Amino-1-[2-[4-(tert-butoxycarbonyl)piperazin-1-yl]ethoxy]-4-(trifluoromethyl)benzeneYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a 1-neck round-bottom flask was added tert-butyl 4-{2-[2-nitro-4-(trifluoromethyl)phenoxy]ethyl}piperazine-1-carboxylate (2.44 g, 0.0058 mol), 5% palladium/carbon (0.20 g), and EtOAc (74 mL). The mixture was allowed to stir under an atmosphere of hydrogen overnight and then filtered through Celite. The filtrate was concentrated to give tert-butyl 4-{2-[2-amino-4-(trifluoromethyl)phenoxy]ethyl}piperazine-1-carboxylate (1.63 g, 68%) as a white solid. LCMS: (FA) ES+390.1.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ccba84b88b5340cfb142bc6fdd9752c3
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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