HCID 59442134, compound → HCID 59441972, compound

HRID 1014177Notes

Reaction equation

HRID 1014177 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O)=[CH2:2]>[Pd].C(O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:19])[CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9])[CH3:2]

Participants

4

Reactant 1

HCID 59442134HCID 59442134, compound

Product 1

HCID 59441972HCID 59441972, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(3-ethenyl-4-nitrophenyl)-4-(1-methylethyl)piperazine (1.4 g, 5.1 mmol) and 10% palladium on carbon (0.5 g) in degassed ethanol was maintained under an atmosphere of hydrogen (60 psi) overnight. The next morning, the reaction was filtered through celite, concentrated, and purified via chromatography on SiO2 to afford 2-ethyl-4-[4-(1-methylethyl)-1-piperazinyl]aniline (0.8 g, 3.2 mmol, 64% Yield). 1H NMR (400 MHz, CDCl3) d ppm 0.92 (t, J=7.3 Hz, 3 H), 1.51-1.60 (m, 2 H), 1.81 (dd, J=7.7, 2.9 Hz, 4 H), 1.98-2.06 (m, 2 H), 2.30-2.37 (m, 2 H), 2.40 (t, J=7.9 Hz, 1 H), 3.06 (d, J=11.7 Hz, 2 H), 3.67 (s, 2 H), 3.82 (s, 3 H), 6.63-6.70 (m, 3 H). 1 H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (d, J=6.6 Hz, 6 H), 1.07 (td, J=7.5, 0.7 Hz, 3H), 2.37 (q, J=7.3 Hz, 2 H), 2.51 (s, 4 H), 2.59-2.67 (m, 1 H), 2.86 (s, 4 H), 4.29 (s, 2 H), 6.48 (s, 1H), 6.51 (d, J=19.0 Hz, 2 H).

Workup

  1. filtrationThe next morning, the reaction was filtered through celite,
  2. concentrationconcentrated
  3. custompurified via chromatography on SiO2

Sources & evidence

ORD record
ord-990d0581e02842208e2765c73f2fbf1f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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