2-Iodohexane → 4-Hydroxy-1-Hexylpiperidine

HRID 1107565

Reaction equation

HRID 1107565 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.I[CH:9]([CH2:11][CH2:12][CH2:13][CH3:14])[CH3:10]>CC(CC)=O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:10][CH2:9][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 330192-IodohexaneHCID 79341Piperidin-4-ol

Product 1

HCID 229236974-Hydroxy-1-HexylpiperidineYield 64%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Hydroxypiperidine (2.02 g, 20 mmol) was dissolved in 100 mL of methyl ethylketone. To this stirred mixture was added 2-iodohexane (1.5 mL, 10 mmol) and the resulting solution was heated at reflux for 1.5 hours. The mixture was allowed to cool and was then washed with saturated aqueous sodium bicarbonate (3×75 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated, and the residue was dried overnight under house vacuum to yield 1.184 g (64%) of the title compound which was used without further purification. 1H NMR consistent with desired product. MS(FD) 186(M+).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto cool
  4. washwas then washed with saturated aqueous sodium bicarbonate (3×75 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue was dried overnight under house vacuum

Sources & evidence

ORD record
ord-e3f26c66634643b08fe45bb101c390a3
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Linked notes

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