Imidazole → Tert-butyl 4-iodopiperidine-1-carboxylate

HRID 2184816Notes

Reaction equation

HRID 2184816 reaction equation
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.O[CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>C(#N)C.C(OCC)C>[I:1][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

86 g of iodine are added at ambient temperature to a suspension of 89 g of triphenylphosphine and 22 g of imidazole in 800 ml of acetonitrile. The reaction is exothermic. After return to ambient temperature, 45.9 g of the product obtained in Step 1 in 250 ml of acetonitrile are added in the course of 30 minutes. After 18 hours stirring at ambient temperature, the reaction mixture is filtered and rinsed with 200 ml of acetonitrile and the resulting filtrate is concentrated in vacuo. The residue obtained is stirred in 250 ml of diethyl ether for 1 hour and the precipitate is filtered off. After concentration of the filtrate in vacuo, chromatography on silica gel (dichloromethane/ethyl acetate: 90/10) enables the expected product to be isolated.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washrinsed with 200 ml of acetonitrile
  3. concentrationthe resulting filtrate is concentrated in vacuo
  4. customThe residue obtained
  5. filtrationthe precipitate is filtered off
  6. customto be isolated

Sources & evidence

ORD record
ord-e41adfe1f06b41dca81825c0b2e7fbc9
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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