tert-Butyl 4-(2-cyanophenyl)piperazine-1-carboxylate → Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

HRID 1419586Notes

Reaction equation

HRID 1419586 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[CH2:16][NH2:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18388395tert-Butyl 4-(2-cyanophenyl)piperazine-1-carboxylate

Product 1

HCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 18476134Acetic acid ethanolSolvent

Procedure

Platinum oxide (200 mg) was added to a solution of 2-[4-(t-butoxycarbonyl)piperazin-1-yl]benzonitrile (2.01 g, 7 mmol) in ethanol-acetic acid (95:5, 35 mL) and the mixture was shaken under hydrogen (50 psi) for 22 h, adding further platinum oxide (1 g) after 4 h. The mixture was filtered through Hyflo, further ethanol (85 mL), acetic acid (15 mL) and platinum oxide (1 g) were added and the mixture was shaken under hydrogen (50 psi) for 6 h., adding further platinum oxide (200 mg) after 2 h. and 4 h. The mixture was filtered through Hyflo and the solvent was evaporated under reduced pressure. Water (50 mL) was added, the pH was adjusted to 10.0 with aqueous potassium carbonate (saturated) and the mixture was extracted with ether (3×50 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the crude title compound as a pale yellow oil (2.03 g, 100%), δH (360 MHz, CDCl3) 7.34-7.08 (4H, m), 3.91 (2H, s), 3.57 (4H, t, J 4.9 Hz), 2.87 (4H, t, J 4.9 Hz), 1.60 (2H, br s), and 1.49 (9H, s).

Workup

  1. filtrationThe mixture was filtered through Hyflo, further ethanol (85 mL), acetic acid (15 mL) and platinum oxide (1 g)
  2. additionwere added
  3. stirringthe mixture was shaken under hydrogen (50 psi) for 6 h.
  4. additionadding further platinum oxide (200 mg) after 2 h.
  5. custom4 h
  6. filtrationThe mixture was filtered through Hyflo
  7. customthe solvent was evaporated under reduced pressure
  8. additionWater (50 mL) was added
  9. extractionthe mixture was extracted with ether (3×50 mL)
  10. dry with materialThe combined organic fractions were dried (MgSO4)
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e633ed42e094880ad38d6ffc3beec83
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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