Triethylamine → N-[4-(benzyloxy)phenyl]-4-(2-tert-butylphenyl)piperazine-1-carboxamide

HRID 534965Notes

Reaction equation

HRID 534965 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:14][CH2:15]2)=[O:35])=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2562684-(Benzyloxy)phenyl isocyanateHCID 516892Sodium BicarbonateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751071N-[4-(benzyloxy)phenyl]-4-(2-tert-butylphenyl)piperazine-1-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 1.76 g, 6.05 mmol), 1-(benzyloxy)-4-isocyanatobenzene (1.50 g, 6.66 mmol) and triethylamine (2.11 mL, 15.1 mmol) in THF (15 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide N-[4-(benzyloxy)phenyl]-4-(2-tert-butylphenyl)piperazine-1-carboxamide (2.65 g, 99%) as a off white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fc7d4ca225a442a7b585a34cd0e6b8bb
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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