HCID 59452727, compound → HCID 59452788, compound

HRID 419638

Reaction equation

HRID 419638 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]1>CCOC(C)=O.CO.C(Cl)Cl>[CH3:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Participants

3

Reactant 1

HCID 59452727HCID 59452727, compound

Product 1

HCID 59452788HCID 59452788, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 21901258Dichloromethane ethyl acetate methanolSolvent

Procedure

1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (0.87 g, 2.64 mmol) was placed in a 100 mL high pressure vessel and dissolved in 60 mL of 1 to 1 to 1 EtOAc/MeOH/DCM. 5 wt % Platinum(sulfided)/C (1.03 g, 0.26 mmol) was added followed quickly by a rubber septum. The vessel was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (60 psi). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step B (0.602 g, 2.01 mmol, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.58 (s, 1H), 6.43 (s, 1H), 4.44 (s, 2H), 3.69 (s, 3H), 3.15-3.23 (m, 4H), 2.90 (s, 3H), 2.77-2.83 (m, 4H), 2.06 (s, 3H).

Workup

  1. customThe vessel was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe next morning the vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-d32f5ea37b6548bda6f89e4ac3b28985
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Linked notes

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