Ethyl 3-methyl-4-(methylamino)-1-piperidinecarboxylate → N,3-Dimethylpiperidin-4-amine

HRID 1063283Notes

Reaction equation

HRID 1063283 reaction equation
C([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH:8]([CH3:14])[CH2:7]1)(OCC)=O>[OH-].[Na+]>[CH3:13][NH:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH:8]1[CH3:14]

Participants

3

Reactant 1

HCID 15725099Ethyl 3-methyl-4-(methylamino)-1-piperidinecarboxylate

Product 1

HCID 22278841N,3-Dimethylpiperidin-4-amine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

1-Carbethoxy-4-methylamino-3-methylpiperidine (4.0 g, 18.34 mmol) was suspended in 5 M NaOH solution (15 ml), stirred at 110° C. for 24 hr, cooled, extracted with ethyl acetate, dried (Na2SO4) and concentrated to dryness to afford 4-methylamino-3-methyl-piperidine. Yield 1.8 g (77%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.92 (dd, 3H), 1.54 (m, 1H), 2.12 (m, 2H), 2.38 (s, 3H), 2.6 (m, 1H), 2.8 (m, 1H), 3.02 (m, 1H), 3.42 (m, 1H), 3.68 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-34de939bd94e44aaa01c207d3be4b240
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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