Piperidine → HCID 11230353, compound

HRID 1818894Notes

Reaction equation

HRID 1818894 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.C(N(CC)CC)C.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(#N)C>[CH3:13][C:4]1[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]2=[C:2]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 11217833HCID 11217833, compound

Product 1

HCID 11230353HCID 11230353, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-chloro-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (250 mg, 1.265 mmol) was suspended in 8 mL of anhydrous acetonitrile and then dropwisely added with 1.0 mL of triethylamine and piperidine (0.19 mL, 1.898 mmol) in this order and heated to reflux for about 3 hours under the nitrogen atmosphere. The mixture was concentrated under reduced pressure, added with 10 mL of a saturated solution of ammonium chloride and 10 mL of distilled water and then extracted twice with 30 mL of methylene chloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (10% EtOAc/MC) was performed on the resulting residue and 296 mg (95%)of 6-methyl-8-piperidine-1-yl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for about 3 hours under the nitrogen atmosphere
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionadded with 10 mL of a saturated solution of ammonium chloride and 10 mL of distilled water
  5. extractionextracted twice with 30 mL of methylene chloride
  6. customThe resulting organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-77a5603dde4044d8ba181d90aaa69ded
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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