HCID 44814403, compound → HCID 58425628, compound

HRID 1966468Notes

Reaction equation

HRID 1966468 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([N+:28]([O-])=O)=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[NH2:28][C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:8])[CH2:10][CH2:11]2)=[CH:20][C:19]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 44814403HCID 44814403, compound

Product 1

HCID 58425628HCID 58425628, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (0.8 g, 2.0 mmol), and palladium on carbon (40 mg, 5%) in 40 ml ethanol was stirred at room temperature under hydrogen atmosphere overnight. The mixture was filtered with the aid of celite. (4-(4-amino-3-(phenylamino)phenyl)piperazin-1-yl)(phenyl)methanone (0.60 g, 80%) was obtained by flash column chromatograph (60% ethyl acetate in hexanes), ant its hydrochloride was made by bubbling HCl gas in ether solution. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 3.24 (s, br, 4H), 3.53 (s, br, 2H), 3.80 (s, br, 2H), 6.81 (d, J=8.1 Hz, 1H), 6.87 (t, J=7.3 Hz, 1H), 7.26-7.49 (m, 11H), 8.56 (s, br, 1H). 13C NMR (125 MHz, DMSO-d6): δ (ppm) 49.4, 107.5, 110.4, 116.6, 120.1, 124.9, 127.0, 128.4, 129.3, 129.6, 135.5, 137.6, 143.1, 169.0.

Workup

  1. filtrationThe mixture was filtered with the aid of celite

Sources & evidence

ORD record
ord-0ec45ba7acbb4d8da562b19aac4e2c5f
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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