Potassium Phosphate, Tribasic → N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamine

HRID 1966455Notes

Reaction equation

HRID 1966455 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[NH:1][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][CH2:15]1)(=[O:18])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 58425640(4-(2-Amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone

Product 1

HCID 46199221N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamineYield 20%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (4-(2-amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone (0.4 g, 1.2 mmol), copper acetate (0.45 g, 2.5 mmol), potassium phosphate (0.26 g, 1.2 mmol), 18-C-6 (31 mg, 0.12 mmol), 4 Å molecular sieves (1.0 g) and phenylboronic acid and pyridine complex (1.4 g, 3.7 mmol) in 30 ml dry dichloromethane was stirred at room temperature overnight. The reaction was quenched with 20 ml water. The mixture was filtered and extracted with ethyl acetate (3×20 ml), followed by drying over anhydrous sodium sulfate. N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzenamine (0.11 g, 20%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.08 (s, br, 4H), 3.70 (s, br, 4H), 6.43 (s, 1H), 7.12-7.75 (m, 11H), 7.77 (d, J=2.4 Hz, 1H), 8.09 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 51.4, 108.9, 115.8, 120.2, 120.7, 123.8, 127.6, 128.5, 129.1, 130.3, 130.5, 135.8, 139.1, 141.1, 145.5, 145.9, 171.1.

Workup

  1. customThe reaction was quenched with 20 ml water
  2. filtrationThe mixture was filtered
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialby drying over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-19b63a587dd74962a329b34d4eda2834
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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