HCID 59464139, compound → HCID 59464112, compound

HRID 1713910Notes

Reaction equation

HRID 1713910 reaction equation
[CH3:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[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]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 59464139HCID 59464139, compound

Product 1

HCID 59464112HCID 59464112, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 1-(3-methyl-5-nitropyridin-2-yl)piperidine-4-carboxylate (2.40 g) was dissolved in EtOH (86 mL), treated with 10% Pd/C (860 mg) and placed under an atmosphere of hydrogen (balloon). LCMS indicated complete reaction at ˜100 mins. The catalyst was filtered off and solvent removed under vacuum to leave a colourless oil (2.16 g). This was used in the next step without further purification. 1H NMR δ 1.58-1.75 (m, 2H), 1.81-1.91 (m, 2H), 2.10 (s, 3H), 2.37-2.50 (m, 1H), 2.55-2.75 (m, 2H), 2.99-3.09 (m, 2H), 3.61 (s, 3H), 6.76 (d, 1H), 7.48 (d, 1H). MS m/e MH+ 250.27.

Workup

  1. customreaction at ˜100 mins
  2. filtrationThe catalyst was filtered off
  3. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-56efa034f1584f5b8ed465efa1d6794a
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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