Potassium Carbonate → methyl N-(p-methoxybenzyl)nipecotate hydrochloride

HRID 262813Notes

Reaction equation

HRID 262813 reaction equation
[NH:1]1[CH2:10][CH2:9][CH2:8][CH:3]([C:4]([O:6][CH3:7])=[O:5])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:17]C(Cl)(Cl)C(O[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=O>C1(C)C=CC=CC=1>[ClH:17].[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:1]2[CH2:10][CH2:9][CH2:8][CH:3]([C:4]([O:6][CH3:7])=[O:5])[CH2:2]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 351626Methyl piperidine-3-carboxylateHCID 13548121(4-Methoxyphenyl)methyl trichloroacetate

Product 1

HCID 14181476methyl N-(p-methoxybenzyl)nipecotate hydrochlorideYield 63.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 23 g of methyl nipecotate, 24.3 g of potassium carbonate, and 52 g of p-methoxybenzyl trichloroacetate in 800 ml of toluene is refluxed under nitrogen for seventy-two hours. The mixture is cooled, the toluene removed in vacuo, the residue dissolved in chloroform, and this solution washed once with 400 ml of aqueous potassium carbonate and then with 400 ml of 10% hydrochloric acid. The chloroform solution is dried and concentrated in vacuo to a viscous brown oil. Trituration of this oil with ethyl acetate affords 30.7 g of methyl N-(p-methoxybenzyl)nipecotate hydrochloride as an off-white crystalline solid. Recrystallization from ethyl acetate yields the analytical sample, m.p. 150°-154°.

Workup

  1. temperatureis refluxed under nitrogen for seventy-two hours
  2. temperatureThe mixture is cooled
  3. customthe toluene removed in vacuo
  4. dissolutionthe residue dissolved in chloroform
  5. washthis solution washed once with 400 ml of aqueous potassium carbonate
  6. dry with materialThe chloroform solution is dried
  7. concentrationconcentrated in vacuo to a viscous brown oil

Sources & evidence

ORD record
ord-e2c61846c1484be784d8a29917bb3253
Source dataset
uspto-grants-1979_05
Patent number
US04154960

Reaction notes

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