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Methanol → 2-Piperidineacetic acid ethyl ester hydrochloride

HRID 1881678
Notes
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Reaction equation

HRID 1881678 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].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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 6212Chloroform2×HCID 75960Ethyl 2-pyridylacetate

Product 1

HCID 242012202-Piperidineacetic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702Ethanol
Solvent

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 under an H2 atmosphere (8 bar) at 40° C. overnight. According to TLC control (silica gel, MC/methanol 95:5), the reaction was not complete, so that further chloroform (15 ml) was added and the mixture was stirred under an H2 atmosphere (8 bar) at 40° C. for a further 2 d (TLC control). After cooling, the catalyst was first removed by filtering over filtering earth and the filtrate was concentrated to dryness in vacuo. The ethyl 2-(piperidin-2-yl)acetate hydrochloride was employed in the next stage without further purification.

Workup

  1. stirringthe mixture was stirred under an H2 atmosphere (8 bar) at 40° C. for a further 2 d (TLC control)
  2. temperatureAfter cooling
  3. customthe catalyst was first removed
  4. filtrationby filtering
  5. filtrationover filtering earth
  6. concentrationthe filtrate was concentrated to dryness in vacuo
  7. customThe ethyl 2-(piperidin-2-yl)acetate hydrochloride was employed in the next stage without further purification

Sources & evidence

ORD record
ord-7701260652c740b399edc0f3d0b34a14
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318769B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes