Potassium Carbonate → tert-Butyl 4-((4-(ethoxycarbonyl)-2-methoxyphenoxy)methyl)piperidine-1-carboxylate

HRID 346548Notes

Reaction equation

HRID 346548 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.O[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=1[O:31][CH3:32].[C:33](=[O:36])([O-])[O-:34].[K+].[K+]>CN(C=O)C>[C:13]([O:34][C:33]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][O:11][C:20]2[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=2[O:31][CH3:32])[CH2:18][CH2:17]1)=[O:36])([CH3:18])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 19081872(Piperidin-4-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 21874806tert-Butyl 4-((4-(ethoxycarbonyl)-2-methoxyphenoxy)methyl)piperidine-1-carboxylateYield 161.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

1-tert-Butoxycarbonyl)-4-(4-methylphenylsulphonyloxymethyl)piperidine (40 g, 0.11 mol), (prepared as described for the starting material in Example 1), was added to a suspension of ethyl 4-hydroxy-3-methoxybenzoate (19.6 g, 0.1 mol) and potassium carbonate (28 g, 0.2 mol) in dry DMF (200 ml). After stirring at 95° C. for 2.5 hours, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate/ether. The organic layer was washed with water, brine, dried (MgSO4) and evaporated. The resulting oil was crystallised from petroleum ether and the suspension was stored overnight at 5° C. The solid was collected by filtration, washed with petroleum ether and dried under vacuum to give ethyl 4(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-3-methoxybenzoate (35 g, 89%).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. custompartitioned between water and ethyl acetate/ether
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resulting oil was crystallised from petroleum ether
  7. waitthe suspension was stored overnight at 5° C
  8. filtrationThe solid was collected by filtration
  9. washwashed with petroleum ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-81e7bd0b28e74333b05ba637db129f38
Source dataset
uspto-grants-2007_02
Patent number
US07173038B1

Reaction notes

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