HCID 59464061, compound → HCID 59464300, compound

HRID 1713916Notes

Reaction equation

HRID 1713916 reaction equation
[CH3:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][C:14](=[C:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CCO.[Pd]>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 59464061HCID 59464061, compound

Product 1

HCID 59464300HCID 59464300, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-[1-(3-methyl-5-nitropyridin-2-yl)piperidin-4-ylidene]propanoate (2.30 g; 7.20 mmol) was suspended in EtOH (100 mL) and treated with 10% Pd/C (230 mg). The resulting mixture was placed under an atmosphere of hydrogen (balloon) at ambient temperature and stirred vigorously at ambient temperature for 2 hrs. LCMS indicated no reduction of alkene but reduction of the nitro-group was essentially complete. The catalyst was filtered off and the filtrate was evaporated to a gum (2.42 g). The reaction was repeated under 20 bar of hydrogen, at 30° C., for 3 hrs with 241 mg 10% Pd/C catalyst. The catalyst was filtered off (Celite) and the solvent removed under vacuum to leave a dark blue gum (2.12 g). This was used in the next step without further purification. 1H NMR δ 1.06 (d, 3H), 1.18 (t, 3H), 1.24-1.43 (m, 2H), 1.45-1.63 (m, 2H), 1.61-1.74 (m, 1H), 2.06 (s, 3H), 2.21-2.35 (m, 1H), 2.50-2.63 (m, 1H), 2.99-3.13 (m, 2H), 3.36-3.50 (m, 1H), 3.98-4.14 (m, 2H), 4.65 (s, 2H), 6.76 (d, 1H), 7.47 (d, 1H). MS m/e MH+ 292.27.

Workup

  1. customwas placed under an atmosphere of hydrogen (balloon) at ambient temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated to a gum (2.42 g)
  4. waitThe reaction was repeated under 20 bar of hydrogen, at 30° C., for 3 hrs with 241 mg 10% Pd/C catalyst
  5. filtrationThe catalyst was filtered off (Celite)
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-6aa231914f334a45aa4d43992d92589c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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