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

HRID 577365Notes

Reaction equation

HRID 577365 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 mixture was filtered and the filtrate was evaporated. The residue was dissolved in water (30 ml) and adjusted to pH10 with a saturated solution of sodium hydrogen carbonate. The mixture was diluted with ethyl acetate/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. The organic layers were washed with water, brine, dried (MgSO4), filtered and evaporated. The resulting solid was triturated in a mixture of ether/petroleum ether, filtered, washed with petroleum ether and dried under vacuum at 60° C. to give ethyl 6-amino-3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (2.58 g, 80%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in water (30 ml)
  4. additionThe mixture was diluted with ethyl acetate/ether (1/1)
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was further extracted with ethyl acetate/ether
  7. washThe organic layers were washed with water, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe resulting solid was triturated in a mixture of ether/petroleum ether
  12. filtrationfiltered
  13. washwashed with petroleum ether
  14. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-e0a506ab6e2a44de9c94ec87e926458a
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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