Dichloromethane → HCID 90041415, compound

HRID 530390Notes

Reaction equation

HRID 530390 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].ClCCl>[Pd].C(OCC)(=O)C.C(O)(=O)C>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[C:15]([NH2:17])[CH:14]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)[CH2:9][CH2:10]1)(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 90041802HCID 90041802, compound

Product 1

HCID 90041415HCID 90041415, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10 wt %, 13 mg, 0.012 mmol) was added to a solution of 1-(methylsulfonyl)-4-(5-nitrobiphenyl-3-yl)piperazine (44.1 mg, 0.122 mmol) in ethyl acetate (1 mL) and acetic acid (0.1 mL) and the reaction mixture was stirred under an atmosphere of H2 (balloon) for 90 minutes. Dichloromethane was added to the reaction mixture, and the mixture was filtered through CELITE, rinsed with ethyl acetate and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to provide 5-[4-(methylsulfonyl)piperazin-1-yl]biphenyl-3-amine as a white foam. 1H NMR (400 MHz, Acetone) δ 9.18 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 7.77-7.63 (m, 3H), 7.47 (dd, J=10.4, 4.7 Hz, 2H), 7.37 (t, J=7.4 Hz, 1H), 7.23 (d, J=4.9 Hz, 1H), 7.02 (d, J=1.5 Hz, 1H), 3.43 (dd, J=12.4, 5.3 Hz, 8H), 2.91 (s, 3H).

Workup

  1. filtrationthe mixture was filtered through CELITE
  2. washrinsed with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6b0146ac928a456a8a97156dd2f87985
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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