4-Ethylamino-1-carbethoxy-3,5-dimethylpiperidine → 4-Ethylamino-3,5-dimethylpiperidine

HRID 746898Notes

Reaction equation

HRID 746898 reaction equation
[CH2:1]([NH:3][CH:4]1[CH:9]([CH3:10])[CH2:8][N:7](C(OCC)=O)[CH2:6][CH:5]1[CH3:16])[CH3:2]>[OH-].[Na+]>[CH2:1]([NH:3][CH:4]1[CH:5]([CH3:16])[CH2:6][NH:7][CH2:8][CH:9]1[CH3:10])[CH3:2]

Participants

3

Reactant 1

HCID 222789054-Ethylamino-1-carbethoxy-3,5-dimethylpiperidine

Product 1

HCID 219737524-Ethylamino-3,5-dimethylpiperidine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The Mixture B of isomers of 4-ethylamino-1-carbethoxy-3,5-dimethylpiperidine (2.1 g, 0.92 mmol) was stirred in 5 N NaOH solution (20 ml) at 100° C. for 96 hr, cooled, extracted with ethyl acetate, dried (Na2SO4) and concentrated to afford Mixture B of isomers 4-ethylamino-3,5-dimethylpiperidine as oil. Yield 1.34 g (93.2%), C9H20N2, m/z 157 (M+1), PMR (CDCl3): 0.94 (dd, 6H), 1.12 (t, 3H), 1.5-1.8 (m, 3H, D2O exchangeable), 1.9 (m, 1H), 2.28 (m, 2H), 2.46 (m, 1H), 2.62-3.0 (m, 4H).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-978b74ca05384cc980a95e5981576cf8
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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