Chloroform → Methyl 3-(2-piperidinyl)propanoate hydrochloride

HRID 1645239

Reaction equation

HRID 1645239 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].C(Cl)(Cl)[Cl:14]>C1COCC1.O=[Pt]=O>[ClH:14].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 53733726Methyl 3-(2-pyridyl)-2-propenoate

Product 1

HCID 47000747Methyl 3-(2-piperidinyl)propanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(pyridin-2-yl)acrylate (22.15 g, 136 mmol) was dissolved in THF (300 ml) and chloroform (10.9 ml), and PtO2 (3.08 g, 13.6 mmol, 0.1 eq.) was added under a nitrogen atmosphere. The solution was first rinsed with nitrogen for 10 min and was then stirred overnight under a H2 atmosphere (8 bar). After cooling, rinsing with nitrogen was first carried out again, the catalyst was removed by filtering over filtering earth and then rinsed with DCM, and the filtrate was concentrated to dryness in vacuo. The methyl 3-(piperidin-2-yl)propionate hydrochloride was used in the next stage without being purified further.

Workup

  1. washThe solution was first rinsed with nitrogen for 10 min
  2. temperatureAfter cooling
  3. washrinsing with nitrogen
  4. customthe catalyst was removed
  5. filtrationby filtering
  6. filtrationover filtering earth
  7. washrinsed with DCM
  8. concentrationthe filtrate was concentrated to dryness in vacuo
  9. customwithout being purified further

Sources & evidence

ORD record
ord-71c88d92b1124036883e326911ef9ce3
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Linked notes

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