Benzyl chloroformate → HCID 22146749, compound

HRID 1823830Notes

Reaction equation

HRID 1823830 reaction equation
[Cl:1]C(O[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH2:12]([NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)C1C=CC=CC=1.C(=O)([O-])O.[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.O>[ClH:1].[CH2:5]([N:23]1[CH2:24][CH2:25][CH:20]([NH:19][CH3:12])[CH2:21][CH2:22]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 3016528N-benzylpiperidin-4-amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 22146749HCID 22146749, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Benzyl chloroformate (4.44 g, 26.0 mmol) in ether (10 ml) was added dropwise to an ether (50 ml) solution of N-benzyl-4-piperidinamine (4.50 g, 23.6 mmol) and aqueous sodium hydrogen carbonate (50 ml) at 0° C. After addition was complete the reaction was warmed to room temperature and the layers separated, the organic layer was washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was dissolved in tetrahydrofuran (80 ml) and lithium aluminium hydride (2.69 g, 70.8 mmol) was added portionwise and the reaction heated under reflux for 12 hours. Upon cooling to 0° C. water (4 ml) was cautiously added followed by 2N sodium hydroxide (4 ml) and the precipitate removed by filtration. The solvent was removed under reduced pressure to yield a yellow oil which was dissolved in ether (100 ml) and hydrogen chloride gas was bubbled through to give a white precipitate. Filtration furnished the title compound as a white solid, 4.30 g.

Workup

  1. additionAfter addition
  2. customthe layers separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (80 ml)
  8. temperaturethe reaction heated
  9. temperatureunder reflux for 12 hours
  10. additionwas cautiously added
  11. customthe precipitate removed by filtration
  12. customThe solvent was removed under reduced pressure
  13. customto yield a yellow oil which
  14. customhydrogen chloride gas was bubbled through
  15. customto give a white precipitate
  16. filtrationFiltration

Sources & evidence

ORD record
ord-c5456a5366dc424697347b94d3fe72ed
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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