Water → HCID 178468171, compound

HRID 2060013Notes

Reaction equation

HRID 2060013 reaction equation
[I-].[CH2:2]([N+:4]1(C)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)[CH3:3].[CH2:12]([O:14][C@H:15]1[CH2:20]C[C@H](N)[CH2:17][CH2:16]1)[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[CH2:12]([O:14][C@H:15]1[CH2:20][CH2:3][C@H:2]([N:4]2[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]2)[CH2:17][CH2:16]1)[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 178468176HCID 178468176, compound

Product 1

HCID 178468171HCID 178468171, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-4-piperidone methiodide (D9, 27 g), trans-4-ethoxycyclohexylamine (D65, 8.16 g, 0.065 mol), potassium carbonate (13.5 g), water (100 mL), and ethanol (200 mL) was heated for 3 hours at 80° C., then cooled overnight. The mixture was partitioned with aqueous sodium bicarbonate and dichloromethane. The dichloromethane layer was separated, washed with brine and solvent removed to give the title compound as an amber coloured oil (13.2 g).

Workup

  1. temperaturecooled overnight
  2. customThe mixture was partitioned with aqueous sodium bicarbonate and dichloromethane
  3. customThe dichloromethane layer was separated
  4. washwashed with brine and solvent
  5. customremoved

Sources & evidence

ORD record
ord-e185523772c842348d129cb2be616376
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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