Ethyl Acetate → HCID 18686769, compound

HRID 1872498Notes

Reaction equation

HRID 1872498 reaction equation
[Cl:1][C:2]1[C:3]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:4]([NH:11]CC2C=CC(OC)=CC=2)[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.CCOC(C)=O>C(Cl)Cl.O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>[NH2:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 18686761HCID 18686761, compound

Product 1

HCID 18686769HCID 18686769, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneSolvent2×

Procedure

To a solution of (3-chloro-6-nitro-2-piperidin-1-ylmethyl-phenyl)-(4-methoxy-benzyl)-amine (22) (0.389 g, 1 mmol) in CH2Cl2 (5 mL) and H2O (0.25 mL), DDQ was added at room temperature under vigorous stirring. The dark reaction mixture was monitored by TLC (SiO2, Hexanes:EtOAc, 8:2) and additional DDQ (0.345 g, 1 mmol) was added. The reaction mixture was filtered after additional 2 hours of stirring and diluted with saturated aqueous NaHCO3 solution (100 mL). The product was extracted with CH2Cl2 (2×100 mL), and the extracts were washed with saturated NaCl solution (2×200 mL) and dried (MgSO4). Dark oil (1.68 g) was chromatographed (SiO2, Hexanes:EtOAc, 9:1 to 8:2) twice to give the desired aniline derivative as a yellow solid. Yield: 0.68 g, 25%. 1H-NMR (CDCl3) δ 1.43 (m, 2H), 1.53 (m, 4H), 2.38 (m, 4H), 3.75 (s, 2H), 6.6 (d, 1H, J=9.2 Hz), 7.95 (d, 1H, J=9.2 Hz). MS (CI) m/z 270 (M+H), 272 (M+2H). Anal Calcd for C12H16N3O2Cl: C, 53.44; H, 5.98; N, 15.58. Found: C, 53.76; H, 5.91; N, 15.01.

Workup

  1. customThe dark reaction mixture
  2. additionwas added
  3. filtrationThe reaction mixture was filtered after additional 2 hours
  4. additiondiluted with saturated aqueous NaHCO3 solution (100 mL)
  5. extractionThe product was extracted with CH2Cl2 (2×100 mL)
  6. washthe extracts were washed with saturated NaCl solution (2×200 mL)
  7. dry with materialdried (MgSO4)
  8. customDark oil (1.68 g) was chromatographed (SiO2, Hexanes:EtOAc, 9:1 to 8:2) twice

Sources & evidence

ORD record
ord-ad8586e2fcaa4a4aa44155115fbb96ac
Source dataset
uspto-grants-2000_08
Patent number
US06110911

Reaction notes

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