Chloroform → 2-PIPERIDINEACETIC ACID, ETHYL ESTER, HYDROCHLORIDE (1:1)

HRID 1645238Notes

Reaction equation

HRID 1645238 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(Cl)(Cl)[Cl:14].C(Cl)Cl.CO>C(O)C.O=[Pt]=O>[ClH:14].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 6212Chloroform2×HCID 75960Ethyl 2-pyridylacetateHCID 21226129Dichloromethane methanol

Product 1

HCID 242012202-PIPERIDINEACETIC ACID, ETHYL ESTER, HYDROCHLORIDE (1:1)

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 2-(pyridin-2-yl)acetate (24.51 g, 148.4 mmol) was dissolved in ethanol (130 ml), and PtO2 (3.37 g, 14.84 mmol, 0.1 eq.) and chloroform (20 ml) were added. The suspension was stirred overnight under a H2 atmosphere (8 bar) at 40° C. According to TLC monitoring (silica gel, DCM/methanol 95:5), the reaction was incomplete, so that further chloroform (15 ml) was added and stirring was carried out for a further 2 d under a H2 atmosphere (8 bar) at 40° C. (TLC monitoring). After cooling, the catalyst was first removed by filtration over filtering earth and the filtrate was concentrated to dryness in vacuo. The ethyl 2-(piperidin-2-yl)acetate hydrochloride was used in the next stage without being purified further. Yield: 31.51 g, >100%

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas carried out for a further 2 d under a H2 atmosphere
  4. customat 40° C.
  5. temperatureAfter cooling
  6. customthe catalyst was first removed by filtration
  7. filtrationover filtering earth
  8. concentrationthe filtrate was concentrated to dryness in vacuo
  9. customwithout being purified further

Sources & evidence

ORD record
ord-dcc53eb7a1924931a6ec925ac4f78bef
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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