Methane → HCID 59441781, compound

HRID 1014264Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][C:11]=2[CH3:21])[CH2:6][CH2:5]1)[CH3:3].NN.C>CO.[Fe](Cl)(Cl)Cl>[CH3:21][C:11]1[C:10]([N:7]2[CH2:6][CH2:5][N:4]([CH:2]([CH3:3])[CH3:1])[CH2:9][CH2:8]2)=[CH:15][C:14]([O:16][CH3:17])=[C:13]([CH:12]=1)[NH2:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(1-methylethyl)-4-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperazine (1.78 g, 6.08 mmol) in methanol (75 mL) was added hydrazine (1.33 mL, 7.0 mmol), iron (III) chloride (0.200 g, 1.22 mmol) and activated charcoal (2 g). The resulting slurry was warmed to 60° C. and maintained overnight. The next morning the slurry was filtered and concentrated to a residue. The residue was partitioned between ethyl acetate and sat. NaCl(aq). The organic layer was washed twice with saturated brine, dried over sodium sulfate, and taken to a residue under reduced pressure to afford 5-methyl-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline (1.50 g, 94% yield) of sufficient purity for use directly in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98 (d, J=6.60 Hz, 6 H), 2.04 (s, 3 H), 2.52 (s, 4 H), 2.64 (dt, J=12.92, 6.55 Hz, 1 H), 2.68-2.72 (m, 4 H), 3.69 (s, 3 H), 4.28 (s, 2 H), 6.41 (s, 1 H), 6.55 (s, 1 H).

Workup

temperaturemaintained overnight
filtrationThe next morning the slurry was filtered
concentrationconcentrated to a residue
customThe residue was partitioned between ethyl acetate and sat. NaCl(aq)
washThe organic layer was washed twice with saturated brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-004df93bb68b4e849e930fceefef134b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

Loading…