1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine → 5-methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepin-1-yl}aniline

HRID 419589Notes

Reaction equation

HRID 419589 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[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:15][CH2:14]1>CCOC(C)=O.CO>[CH3:1][C:2]1[C:3]([N:13]2[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:23])=[O:24])[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 598602621-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine

Product 1

HCID 594529115-methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepin-1-yl}anilineYield 91%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine (0.70 g, 1.9 mmol) was placed in a 200 mL high pressure vessel and dissolved in 40 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/C (0.51 g, 0.132 mmol) was added followed quickly by a rubber septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (60 psi). The solution stirred for 2 h. 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 C (0.585 g, 1.71 mmol, 91%). 1H NMR (400 MHz, DMSO-d6) δ 6.54 (s, 1H), 6.38 (s, 1H), 4.27 (br. s., 2H), 3.67 (s, 3H), 3.24 (t, J=6.59 Hz, 2H), 3.02 (s, 3H), 2.86-2.97 (m, 6H), 2.75 (t, J=5.49 Hz, 2H), 2.68-2.73 (m, 2H), 2.05 (s, 3H), 1.74-1.81 (m, 2H).

Workup

  1. customThe vial was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe 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-16d1e0d72cb748a796e8670e7b938983
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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