Triethylamine → 3-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamine

HRID 1966466Notes

Reaction equation

HRID 1966466 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:4]2[CH:3]=[C:2]([NH:1][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:13][CH2:12]1)(=[O:15])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 28800116(4-(3-Aminophenyl)piperazin-1-yl)(phenyl)methanone

Product 1

HCID 584256333-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamineYield 66%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (4-(3-aminophenyl)piperazin-1-yl)(phenyl)methanone (0.5 g, 1.8 mmol), copper acetate (0.65 g, 3.6 mmol), triethylamine (1.7 ml, 12.4 mmol), 4 Å molecular sieves (0.5 g) and phenylboronic acid and pyridine complex (0.70 g, 1.8 mmol) in 30 ml dry dichloromethane was stirred at room temperature overnight. The reaction was quenched with 20 ml water extracted with dichloromethane (3×40 ml), followed by drying over anhydrous sodium sulfate. 3-(4-Benzoylpiperazin-1-yl)-N-phenylbenzenamine (0.42 g, 66%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.20 (d, br, 4H), 3.65 (d, br, 4H), 5.73 (s, 1H), 6.54 (dd, J=8.0, 1.6 Hz, 1H), 6.67 (m, 2H), 6.97 (t, J=7.4 Hz, 1H), 7.11 (dd, J=8.6, 1.0 Hz, 2H), 7.28 (t, J=8.0 Hz, 1H), 7.44 (m, 2H), 7.48 (m, 5H). 13C NMR (125 MHz, CDCl3): δ (ppm) 50.0, 50.1, 50.3, 106.5, 110.0, 110.7, 118.6, 121.6, 127.6, 129.0, 129.8, 130.3, 130.5, 136.1, 143.5, 144.7, 152.6, 170.9.

Workup

  1. customThe reaction was quenched with 20 ml water
  2. extractionextracted with dichloromethane (3×40 ml)
  3. dry with materialby drying over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-69ffd6eefbc7440b83f6d062676b7f00
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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