1-Boc-4-(4-Nitrophenyl)piperazine → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 743693Notes

Reaction equation

HRID 743693 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-(N-tert-butyloxycarbonyl-N'-piperazinyl)-1-nitrobenzene (3.09 g) in ethanol (70 ml) was hydrogenated at 30 psi for 15 min, in the presence of a palladium on carbon catalyst (0.35 g, 11% (w/w)). The catalyst was filtered off and the residue evaporated in vacuo. The resultant oil was azeotroped with toluene (2×20 ml) followed by petrol (60/80) (20 ml) to afford the aniline (1.96 g). 1H NMR (360 MHz, CDCl3) δ 1.48 (9H, s), 2.96-2.98 (4H, m), 3.56-3.59 (4H, m), 6.65 (2H, d, J=8.7), 6.81 (2H, d, J=8.7 Hz). MS (CI, NH3) 278 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe residue evaporated in vacuo
  3. customThe resultant oil was azeotroped with toluene (2×20 ml)

Sources & evidence

ORD record
ord-1cfbe140cd4e42719b57e1cc61b43cf5
Source dataset
uspto-grants-1996_09
Patent number
US05556969

Reaction notes

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