Piperidine → HCID 22710373, compound

HRID 352820Notes

Reaction equation

HRID 352820 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][CH:22]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][CH2:22][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 22709781HCID 22709781, compound

Product 1

HCID 22710373HCID 22710373, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 mL) were dissolved 1,4-dibenzyl-2-(formylmethyl)piperazine (600 mg) and piperidine (200 mg). After stirring for 30 minutes, the solvent was concentrated under reduced pressure. The concentrate was dissolved in methanol (10 mL), followed by the addition of sodium borohydride (147 mg). The resulting mixture was stirred. Five hours later, the solvent was distilled off under reduced pressure. Chloroform was added to the residue and the mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=10:1→5:1), whereby the title compound (640 mg) was obtained as a colorless oil.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in methanol (10 mL)
  3. additionfollowed by the addition of sodium borohydride (147 mg)
  4. stirringThe resulting mixture was stirred
  5. distillationFive hours later, the solvent was distilled off under reduced pressure
  6. additionChloroform was added to the residue
  7. washthe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=10:1→5:1), whereby the title compound (640 mg)
  12. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-80d2a91bf49e45c695a99b20c6f059ea
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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