Imidazole → Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 399430Notes

Reaction equation

HRID 399430 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:41]I>C1C=CC=CC=1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][I:41])[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 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-11 (10.42 g, 0.048 mol) was dissolved in 400 ml benzene, imidazole (4.66 g, 0.068 mol), triphenylphosphine (15.24 g, 0.05 mol) and iodine (0.048 mol) were added at room temperature. After 6 hours the reaction mixture was filtered and the filtrate was evaporated to give a dark residue. This was purified by flash chromatography on silica gel eluting with 10% EtOAc-hexanes to give 2-12 as a yellow oil.

Workup

  1. filtrationAfter 6 hours the reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give a dark residue
  4. customThis was purified by flash chromatography on silica gel eluting with 10% EtOAc-hexanes

Sources & evidence

ORD record
ord-2945ba3d69794499b84bedc555d8ce7e
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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