Methanol → 4-Amino-piperidine-4-carboxylic acid methyl ester 2HCl

HRID 264307Notes

Reaction equation

HRID 264307 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:13]O>>[ClH:1].[ClH:1].[NH2:3][C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 887MethanolHCID 229070884-Aminopiperidine-4-carboxylic acid--hydrogen chloride (1/2)

Product 1

HCID 229072144-Amino-piperidine-4-carboxylic acid methyl ester 2HCl

Procedure

Into a heterogeneous mixture of 4-amino-4-carboxypiperidine dihydrochloride (61.0 g, 0.34 mmol) in methanol (600 mL) is bubbled hydrogen chloride gas at room temperature. The reaction mixture is concentrated to dryness in vacuo, dissolved in 1,4-dioxane (200 mL), and concentrated in vacuo. The residue is redissolved in methanol (1600 mL) into which hydrogen chloride gas is bubbled for 45 minutes. The reaction mixture is refluxed for 18 hours. Most of the solvent is then evaporated, the product is collected by filtration, and washed with ethyl acetate to give 4-amino-4-carbomethoxypiperidine dihydrochloride.

Workup

  1. customis bubbled hydrogen chloride gas at room temperature
  2. concentrationThe reaction mixture is concentrated to dryness in vacuo
  3. dissolutiondissolved in 1,4-dioxane (200 mL)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is redissolved in methanol (1600 mL) into which hydrogen chloride gas
  6. customis bubbled for 45 minutes
  7. temperatureThe reaction mixture is refluxed for 18 hours
  8. customMost of the solvent is then evaporated
  9. filtrationthe product is collected by filtration
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3694f89379a941b8b090c9220f1ff57a
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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