Tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylate → Tert-butyl 4-(2-(3,4-diaminophenoxy)ethyl)piperazine-1-carboxylate

HRID 415113Notes

Reaction equation

HRID 415113 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[N+:24]([O-])=O>[Pd].C(O)C>[NH2:24][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:2]=1[NH2:1])[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

Participants

4

Reactant 1

HCID 66623212Tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylate

Product 1

HCID 59349631Tert-butyl 4-(2-(3,4-diaminophenoxy)ethyl)piperazine-1-carboxylateYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A hydrogenation vessel was charged with tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylate (1.74 g, 4.76 mmol), ethanol (100 mL) and 10% palladium on charcoal (w/w 50% water) (1 g). The reaction vessel was shaken on a Parr Hydrogenation under an atmosphere of hydrogen gas (40 psi). The reaction was completed in 2 hours as determined by LCMS. The reaction mixture was filtered through a plug of Celite and washed with methanol. The filtered was evaporated under pressure to give 1.53 g of tert-butyl 4-(2-(3,4-diaminophenoxy)ethyl)piperazine-1-carboxylate (95% yield) and was used in the next step without any further purification. MS (EI): 337 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washwashed with methanol
  3. customThe filtered was evaporated under pressure

Sources & evidence

ORD record
ord-12a107606a9941b2baa3f860082b8ba9
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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