1-Piperidinecarboxaldehyde → HCID 15132179, compound

HRID 1656927Notes

Reaction equation

HRID 1656927 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH3:16].[CH:17](N1CCCCC1)=[O:18]>O1CCCC1.BrCBr>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:17]=[O:18])[C:10]=1[CH3:16]

Participants

5

Reactant 2

HCID 174291-PiperidinecarboxaldehydeHCID 15132178HCID 15132178, compound

Product 1

HCID 15132179HCID 15132179, compound

Reagents, catalysts & solvents 2

HCID 3024DibromomethaneCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1.2 g of Mg (magnesium shavings) in 15 ml of absolute tetrahydrofuran are initially introduced under a nitrogen atomsphere. A few drops of dibromomethane are added at 65° C. A solution of 14.25 g of 3-bromo-2-methylbenzyl tetrahydro-2-pyranyl ether in 50 ml of tetrahydrofuran is added dropwise while the temperature is kept at 65° C. The refluxed mixture is then stirred for 2 hours. A solution of 5.65 g of N-formylpiperidine in 10 ml of absolute tetrahydrofuran is added dropwise to the reaction mixture after the latter has been cooled to 0° C. Stirring is carried out for 20 hours at room temperature, the mixture is rendered slightly acidic with about 50 ml of 5% strength hydrochloric acid and extraction is carried out several times with ether. The combined ether extracts are washed with water, dried and evaporated down. The crude product (11 g) can be purified by column chromatography over silica gel using 97.5:2.5 toluene/acetone.

Workup

  1. customis kept at 65° C
  2. stirringStirring
  3. waitis carried out for 20 hours at room temperature
  4. extractionthe mixture is rendered slightly acidic with about 50 ml of 5% strength hydrochloric acid and extraction
  5. washThe combined ether extracts are washed with water
  6. customdried
  7. customevaporated down
  8. customThe crude product (11 g) can be purified by column chromatography over silica gel using 97.5:2.5 toluene/acetone

Sources & evidence

ORD record
ord-b21cf8b4c7c643cc9233e16f0c274704
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Reaction notes

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