Imidazole → 4-(4-Imidazol-1-yl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1157177Notes

Reaction equation

HRID 1157177 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](I)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[N:27]1[C:40]2C(=CC=C3[C:39]=2[N:38]=[CH:37]C=C3)C=CC=1.N1C=CN=C1>CN(C=O)C>[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:38]3[CH:39]=[CH:40][N:27]=[CH:37]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 2795511Tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylate

Product 1

HCID 589851154-(4-Imidazol-1-yl-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 156.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

4-(4-Iodo-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.194 g, 0.5 mmol), Cul (0.01 g), Cs2CO3 (0.326 g, 1.0 mmol), [1,10]Phenanthroline (0.027 g, 0.15 mmol) and imidazole (0.034 g, 0.5 mmol) were mixed in 3 mL dry DMF in a pressure vessel. The vessel was heated at 110° C. overnight. After cooling to rt, the insoluble was filtered and washed with CH2Cl2. The filtrate was concentrated and the crude was purified with prep TLC (7.5% MeOH-2M NH3/CH2Cl2) to yield the title compound (0.077 g). M+H 328.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe insoluble was filtered
  3. washwashed with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customthe crude was purified with prep TLC (7.5% MeOH-2M NH3/CH2Cl2)

Sources & evidence

ORD record
ord-0d96d1e29a4a4569849366cb028e3049
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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