Ethyl 5-methoxy-4-((1-methylpiperidin-4-yl)methoxy)-2-nitrobenzoate → Ethyl 2-amino-5-methoxy-4-((1-methylpiperidin-4-yl)methoxy)benzoate

HRID 2233255Notes

Reaction equation

HRID 2233255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([N+:23]([O-])=O)=[CH:12][C:13]=1[O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[H][H]>CO.[Pt]>[NH2:23][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[C:13]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH:12]=1

Participants

5

Reactant 2

HCID 21874808Ethyl 5-methoxy-4-((1-methylpiperidin-4-yl)methoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 21874813Ethyl 2-amino-5-methoxy-4-((1-methylpiperidin-4-yl)methoxy)benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A suspension of ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)-6-nitrobenzoate (3.89 g, 10 mmol) in methanol (80 ml) containing 10% platinum on activated carbon (50% wet) (389 mg) was hydrogenated at 1.8 atmospheres pressure until uptake of hydrogen ceased. The reaction was filtered through celite, the filtrate was evaporated and the residue was taken up in water (30 ml) and adjusted to pH10 with a saturated solution of sodium hydrogen carbonate. The mixture was diluted with ethyl acetate/diethyl ether (1:1) and the organic layer was separated. The aqueous layer was further extracted with ethyl acetate/ether and the organic layers were combined prior to washing with water and brine. Solvent evaporation in vacuo, followed by trituration with a mixture of diethyl ether/isohexane yielded ethyl 6-amino-3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (2.58 g, 80% yield) as a white solid after drying in vacuo:

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe filtrate was evaporated
  3. additionThe mixture was diluted with ethyl acetate/diethyl ether (1:1)
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was further extracted with ethyl acetate/ether
  6. washto washing with water and brine
  7. customSolvent evaporation in vacuo
  8. additionfollowed by trituration with a mixture of diethyl ether/isohexane

Sources & evidence

ORD record
ord-b93c37471b084469865f7fec6f467177
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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