Methanol → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 906045Notes

Reaction equation

HRID 906045 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.CO>[Pd].CCOC(C)=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd on C 10% (0.3% p/p) was added to a solution of tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (1 eq) in a mixture (1:1 ratio) MeOH:EtOAc (0.03 M). The atmosphere in the reaction vessel was charged with H2 (1 atm.) and the reaction stirred vigorously for 2 h. At this time, the reaction mixture was filtered through a pad of celite and concentrated in vacuo to afford the title compound (quant); MS (ES+) m/z 278 (M+H)+

Workup

  1. additionThe atmosphere in the reaction vessel was charged with H2 (1 atm.)
  2. filtrationAt this time, the reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3d4893949ca48a5a2e0b5c5e9e4e01a
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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