Benzyl Bromide → Methyl 1-benzyl-2-piperidineacetate

HRID 269720Notes

Reaction equation

HRID 269720 reaction equation
Cl.[C:2]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]1)([O:4][CH3:5])=[O:3].C(N(CC)CC)C.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH2:20]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[CH2:6][C:2]([O:4][CH3:5])=[O:3])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 13778732Methyl 2-(piperidin-2-yl)acetate hydrochloride

Product 1

HCID 21574365Methyl 1-benzyl-2-piperidineacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 13 ml of acetonitrile was dissolved 1.0 g (5.16 mol) of 2-carbomethoxymethylpiperidine hydrochloride, and 1.77 ml (12.72 mmol) of triethylamine and 0.76 ml (6.36 mmol) of benzyl bromide were added to the solution at room temperature, and the resulting mixture was reacted at the same temperature under stirring for 5 hours. After completion of the reaction, the obtained reaction mixture was filtered and then concentrated under reduced pressure, then, 25 ml of ethyl acetate and 15 ml of a saturated aqueous sodium hydrogen carbonate solution were added to the residue and the organic layer was extracted. The obtained organic layer was washed with 15 ml of a saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution, dried over anhydrous magnesium sulfate, then, filtered and the filtrate was concentrated under reduced pressure to obtain 0.97 g of an oily substance. The resulting oily substance was purified by silica gel column chromatography (WAKOGEL C-200 (trade name), n-hexane/ethyl acetate=4/1(volume ratio)) to obtain 0.75 g (Isolated yield based on 2-carbomethoxymethylpiperidine hydrochloride=59%) of N-benzyl-2-carbomethoxymethylpiperidine.

Workup

  1. additionwere added to the solution at room temperature
  2. customthe resulting mixture was reacted at the same temperature
  3. customAfter completion of the reaction
  4. customthe obtained reaction mixture
  5. filtrationwas filtered
  6. concentrationconcentrated under reduced pressure
  7. addition25 ml of ethyl acetate and 15 ml of a saturated aqueous sodium hydrogen carbonate solution were added to the residue
  8. extractionthe organic layer was extracted
  9. washThe obtained organic layer was washed with 15 ml of a saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customto obtain 0.97 g of an oily substance
  14. customThe resulting oily substance was purified by silica gel column chromatography (WAKOGEL C-200 (trade name), n-hexane/ethyl acetate=4/1(volume ratio))
  15. customto obtain 0.75 g (Isolated yield based on 2-carbomethoxymethylpiperidine hydrochloride=59%) of N-benzyl-2-carbomethoxymethylpiperidine

Sources & evidence

ORD record
ord-26d19c6b65d94709b3157346c3228461
Source dataset
uspto-grants-2008_11
Patent number
US07449325B2

Reaction notes

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