Benzyl 2,4-diphenylpiperazine-1-carboxylate → 1,3-Diphenylpiperizine

HRID 473819Notes

Reaction equation

HRID 473819 reaction equation
[C:1]1([CH:7]2[CH2:12][N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][N:8]2C(OCC2C=CC=CC=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.CO.[Pd]>[C:13]1([N:11]2[CH2:10][CH2:9][NH:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 67506058Benzyl 2,4-diphenylpiperazine-1-carboxylate

Product 1

HCID 541766051,3-DiphenylpiperizineYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of benzyl 2,4-diphenylpiperazine-1-carboxylate (0.17 g, 0.45 mmol) and 5% Pd on carbon (0.1 g) in tetrahydrofuran/methanol 5:1 (10 mL) was stirred under hydrogen (1 atm) for 4.5 hours. The reaction was filtered through celite and concentrated to give the title compound 1,3-diphenylpiperizine (0.10 g, 93% yield) as an oil. MS (EI) for C16H18N2: 239 (MH+).

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c3b99b9973024e79808dd94f102614a0
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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