HCID 46199062, compound → HCID 58425595, compound

HRID 1966472Notes

Reaction equation

HRID 1966472 reaction equation
[CH3:1][N:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[N+:23]([O-])=O>C(O)C.[Pt]=O>[CH3:1][N:2]([C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:22])[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH2:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 46199062HCID 46199062, compound

Product 1

HCID 58425595HCID 58425595, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A suspension of N-methyl-5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (0.5 g, 1.2 mmol), and platinum oxide (25 mg, 5%) in 20 ml ethanol was stirred at room temperature under hydrogen atmosphere overnight. The mixture was filtered with the aid of celite. (4-(3-(N-methyl-N-phenylamino)-4-aminophenyl)piperazin-1-yl)(phenyl)methanone (0.42 g, 90%) was obtained by flash column chromatograph (60% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.98 (d, br, 4H), 3.24 (s, 3H), 3.58 (s, br, 2H), 3.63 (s, br, 2H), 3.94 (s, br, 2H), 6.68 (d, J=7.9 Hz, 2H), 6.73 (d, J=2.2 Hz, 1H), 6.82 (m, 3H), 7.23 (m, 2H), 7.45 (s, 5H). 13C NMR (125 MHz, CDCl3): δ (ppm) 39.1, 51.8, 113.9, 117.4, 117.8, 118.1, 118.2, 129.0, 129.6, 127.6, 130.2, 135.3, 136.2, 138.8, 145.2, 149.2, 170.8.

Workup

  1. filtrationThe mixture was filtered with the aid of celite

Sources & evidence

ORD record
ord-46115a9a0651441c926c821f77ff3dd4
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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