Imidazole → Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

HRID 1957575Notes

Reaction equation

HRID 1957575 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClP(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CN=C1.[I:37]I>C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][I:37])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 66180ChlorodiphenylphosphineHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Product 1

HCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of 3-3 (22.7 g, 93 mmol), chlorodiphenylphosphine (21.7 mL, 0.12 mol), imidazole (19.0 g, 0.28 mol), and toluene (300 mL) at 0° C. was added iodine (30.6 g, 0.12 mol) in toluene (700 mL) followed by removal of the cooling bath. After 2.0 h the reaction mixture was washed with saturated Na2CO3, 5% Na2S2O3, 10% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 30% EtOAc/hexanes) gave 3-4 as a colorless oil, RF 0.41 (silica, 10% EtOAc/hexanes.

Workup

  1. customfollowed by removal of the cooling bath
  2. washAfter 2.0 h the reaction mixture was washed with saturated Na2CO3, 5% Na2S2O3, 10% KHSO4 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b9c470125314a8dbb696ffe62d5d590
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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