Sodium Hydroxide → HCID 21922677, compound

HRID 1292121Notes

Reaction equation

HRID 1292121 reaction equation
C([C@@H:5]1[CH2:10][N:9]([CH2:11][CH2:12][CH3:13])[C@@H:8]([CH3:14])[CH2:7][C:6]1=[O:15])(OC)=O.[OH-].[Na+]>Cl>[CH3:14][CH:8]1[CH2:7][C:6](=[O:15])[CH2:5][CH2:10][N:9]1[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86752621HCID 86752621, compound

Product 1

HCID 21922677HCID 21922677, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 6.5 g of predominantly (±)-trans-5-carbomethoxy-2-methyl-4-oxo-1-propyl piperidine and 30 mL of 20% hydrochloric acid was heated to reflux for 2 h. The solution was cooled in an ice bath, basified by addition of NaOH pellets until the pH was 9-10 and extracted with 5×100 mL of chloroform. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. After azeotropic dying with toluene there was obtained 5.6 g of predominantly (±)-2-methyl-4-oxo-1-propyl piperidine as an amber oil: TLC (EtOAc); 1H NMR (400 MHz, CDCl3) 3.1 (m, 1H), 2.9 (m, 1H), 2.8-2.6 (complex m, 3H), 2.5 (m, 4H), 1.5 (m, 2H), 1.15 (d, 3H), 0.9 (t, 3H).

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe solution was cooled in an ice bath
  3. extractionextracted with 5×100 mL of chloroform
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f322ef63b9de4430a6ba5262e166da43
Source dataset
uspto-grants-1998_05
Patent number
US05756508

Reaction notes

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