Piperidine → 1-(4-Iodobenzoyl)piperidine

HRID 1726881Notes

Reaction equation

HRID 1726881 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=[N:35][C:30]2C=[CH:32][CH:33]=[CH:34][C:29]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCCCC1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:35]2[CH2:32][CH2:33][CH2:34][CH2:29][CH2:30]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 120854-Iodobenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 51492041-(4-Iodobenzoyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4.0 g of 4-iodobenzoic acid (16.13 mmol) in 40 ml of CH2Cl2 there are added 3.65 ml of diisopropylethylamine (20.97 mmol) and then, after 10 minutes, 5.18 g of TBTU (16.13 mmol). After stirring for 10 minutes more, 1.60 ml of piperidine (16.13 mmol) are added and the reaction mixture is stirred overnight at ambient temperature. The reaction mixture is washed 3 times with water and then once with saturated NaCl. After drying (MgSO4) and evaporation under reduced pressure, the residue is chromatographed on silica (CH2Cl2/acetone 9/1) to yield the title product.

Workup

  1. stirringthe reaction mixture is stirred overnight at ambient temperature
  2. washThe reaction mixture is washed 3 times with water
  3. customAfter drying
  4. custom(MgSO4) and evaporation under reduced pressure
  5. customthe residue is chromatographed on silica (CH2Cl2/acetone 9/1)

Sources & evidence

ORD record
ord-d608cb7ddaa847de967183dd61927261
Source dataset
uspto-grants-2009_02
Patent number
US07494994B2

Reaction notes

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