Sodium Iodide → HCID 20361138, compound

HRID 2398862Notes

Reaction equation

HRID 2398862 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[I-].[Na+].ICCCCC(OC)=O.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C1C=CC=CC=1.CC(C)=O>[N:21]1([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 274413Methyl 5-chloropentanoateHCID 334445methyl 5-iodopentanoate2×

Product 1

HCID 20361138HCID 20361138, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

A mixture of 0.167 mole of methyl δ-chlorovalerate and 0.25 mole of sodium iodide in 120 ml. of acetone is stirred and heated at reflux for 16 hours. After cooling the mixture, a solid is removed by suction filtration, and the acetone is distilled off using a rotary evaporator. The residue is dissolved in 300 ml. of diethyl ether, and additional solid is removed by filtration. The ethereal solution is washed twice with a 10% sodium thiosulfate solution, one with water and dried over sodium sulfate. The ether is evaporated and the residue distilled at b.p. 107°-110° C. (15 mm.) to give 30.0 g. (74%) of methyl δ-iodovalerate as a light yellow liquid. 30.0 g. (0.124 mole) of methyl δ-iodovalerate and 42.5 g. (0.50 mole) of piperidine are dissolved in 250 ml. of benzene and heated at 60° C. for 3 hours with stirring. A colorless solid begins to appear shortly after the materials are combined. The solid is removed by suction filtration, and the benzene evaporated to give methyl δ-piperidinovalerate which distills as 23.5 g. (95%) of colorless liquid, b.p., 122°-24° C. (12.5 mm.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling the mixture
  4. customa solid is removed by suction filtration
  5. distillationthe acetone is distilled off
  6. customa rotary evaporator
  7. dissolutionThe residue is dissolved in 300 ml
  8. customof diethyl ether, and additional solid is removed by filtration
  9. washThe ethereal solution is washed twice with a 10% sodium thiosulfate solution, one with water
  10. dry with materialdried over sodium sulfate
  11. customThe ether is evaporated
  12. distillationthe residue distilled at b.p. 107°-110° C. (15 mm.)
  13. customto give 30.0 g
  14. customThe solid is removed by suction filtration
  15. customthe benzene evaporated

Sources & evidence

ORD record
ord-2561b42d2f6146fbaed2f3df28c46b62
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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