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3-Carbethoxy-2-piperidone → HCID 71254295, compound

HRID 473329
Notes
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Reaction equation

HRID 473329 reaction equation
[CH3:1][CH:2]1[CH2:7][C@H:6]([OH:8])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[O:12]=[C:13]1[CH:18]([C:19](OCC)=[O:20])[CH2:17][CH2:16][CH2:15][NH:14]1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[O:12]=[C:13]1[CH:18]([C:19]([O:8][C@H:6]2[CH2:7][C@@H:2]([CH3:1])[CH2:3][CH2:4][C@@H:5]2[CH:9]([CH3:11])[CH3:10])=[O:20])[CH2:17][CH2:16][CH2:15][NH:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 977733-Carbethoxy-2-piperidoneHCID 12285346(+) Menthol

Product 1

HCID 71254295HCID 71254295, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

4-Dimethylaminopyridine (0.35 wt), (+)-menthol (0.95 wt) and ethyl 2-oxo-3-piperidinecarboxylate (1 wt) are dissolved/suspended in toluene (10 vol). The mixture is heated to reflux and stirred for seven days with periodic distillation of solvent and replenishment with fresh toluene. The reaction mixture is cooled to 25° C. and washed with two portions of 5% w/w aqueous HCl (4 vol) and then water (4 vol). The organic phase is concentrated under reduced pressure to give the title compound as a colourless oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. washwashed with two portions of 5% w/w aqueous HCl (4 vol)
  4. concentrationThe organic phase is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1b2db29ee2c425c9bc95550352b54b8
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633319B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes