HCID 18457684, compound → N-isopropylpiperidine

HRID 1272519Notes

Reaction equation

HRID 1272519 reaction equation
[CH2:1]=[CH:2][CH3:3].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.CC(O)=O.[Pt](=O)=O>[CH:2]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([CH3:3])[CH3:1]

Participants

5

Reactant 1

HCID 18457684HCID 18457684, compound

Product 1

HCID 240410N-isopropylpiperidineYield 137.9%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of O-protected pyridine propene (1.5 g, 5.7 mmol) and platinum(IV) oxide (258 mg) in MeOH (20 mL) and AcOH (4 ml) was hydrogenated 6 h at 40 psi. The final solution was filtered over Celite, rinsing with MeOH then concentrated. The residue was diluted with 1 N NaOH, extracted with DCM and AcOEt, and combined organic layers were dried over Na2SO4 and concentrated. The residue was quickly passed through a plug of silica gel (eluting hexanes/AcOEt 8:2) to provide 1.0 g (65%) of O-protected isopropyl piperidine.

Workup

  1. filtrationThe final solution was filtered over Celite
  2. washrinsing with MeOH
  3. concentrationthen concentrated
  4. additionThe residue was diluted with 1 N NaOH
  5. extractionextracted with DCM and AcOEt
  6. dry with materialwere dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-27bad28b3dd445d88217f1c0d4fafe7f
Source dataset
uspto-grants-2007_04
Patent number
US07208602B2

Reaction notes

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