Hydrochloric Acid → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 1990912Notes

Reaction equation

HRID 1990912 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].Cl>CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1 equiv of 43 dissolved in methanol (anhydrous) and 10% of 10% Pd/C was added under a hydrogen atmosphere and allowed to stir overnight at room-temp. Reaction was filtered through a pad of celite and concentrated to give a blue/purple oil. The oil was brought up in DCM acidified using 1 M HCl and organic wash was removed. The aqueous was neutralized with sat'd sodium bicarbonate and washed 3 times with DCM, dried with sodium sulfate, filtered and concentrated and resulted in a pale red oil, 72% yield. MS (ES) 277.8 [MH+].

Workup

  1. customReaction
  2. filtrationwas filtered through a pad of celite
  3. concentrationconcentrated
  4. customto give a blue/purple oil
  5. washorganic wash
  6. customwas removed
  7. washwashed 3 times with DCM
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customresulted in a pale red oil, 72% yield

Sources & evidence

ORD record
ord-77cb72ad2ba744e4ba8824cfb4e5d00d
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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