Piperidine → 1-(4-Iodobenzyl)piperidine

HRID 750987Notes

Reaction equation

HRID 750987 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[I:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>ClCCl>[N:1]1([CH2:21][C:20]2[CH:23]=[CH:24][C:17]([I:16])=[CH:18][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9542584-Iodobenzyl bromide

Product 1

HCID 75376001-(4-Iodobenzyl)piperidineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.31 g of piperidine (3.6 mmol) and 0.47 g of N,N-diisopropylethylamine 3.6 mmol) in 10 mL of dichloromethane was added 0.90 g of 4-iodobenzylbromide (3 mmol). The mixture was allowed to stir for 16 h and partitioned between 50 mL of EtOAc and 50 mL of water. The layers were separated and the EtOAc was washed with 25 mL of brine, dried (MgSO4) and concentrated in vacuo to give 0.90 g of 4-(N-piperidinylmethyl)iodobenzene. The product was used without further purification.

Workup

  1. custompartitioned between 50 mL of EtOAc and 50 mL of water
  2. customThe layers were separated
  3. washthe EtOAc was washed with 25 mL of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59030196d9cc42f38bf449ac9db20efa
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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