Imidazole → 4-(N-BOC-Piperidin-4-yl)butyl iodide

HRID 1957580Notes

Reaction equation

HRID 1957580 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:43]I>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][I:43])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 2784670tert-Butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate

Product 1

HCID 193480344-(N-BOC-Piperidin-4-yl)butyl iodideYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-2 (3.4 g, 13.2 mmol), Ph3P (5.2 g, 19.8 mmol), imidazole (2.7 g, 39.6 mmol), and THF (30 mL) at ambient temperature was treated with iodine (5.0 g, 19.8 mmol) in three portions. After 1 h most of the THF was evaporated and the residue partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, 10% Na2S2O3, and brine, dried (MgSO4) and concentrated to give a solid. Flash chromatography (silica, 10% EtOAc/hexanes) gave 4-3 (3.0 g) as a light yellow oil. Rf 0.27 (silica, 10% EtOAc/hexanes).

Workup

  1. customAfter 1 h most of the THF was evaporated
  2. customthe residue partitioned between EtOAc and H2O
  3. washThe EtOAc layer was washed with H2O, 10% Na2S2O3, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a solid

Sources & evidence

ORD record
ord-b79948865628445daa2936700ec6e6a2
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

Loading…