Iodobenzene → HCID 69074101, compound

HRID 1916636Notes

Reaction equation

HRID 1916636 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:27]1([CH2:33][CH:34]([OH:36])[CH3:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:36][CH:34]([CH3:35])[CH2:33][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 233605alpha-Methyl-1-piperidineethanol

Product 1

HCID 69074101HCID 69074101, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.54 g (7.00 mmol) iodobenzene and 2.75 g (10.5 mmol) triphenylphosphane are added successively to a solution of 1.00 g (6.98 mmol) 1-piperidin-1-yl-propan-2-ol in 20 mL DCM. 2.19 mL (10.5 mmol, 95%) diisopropyl azodicarboxylate is added dropwise at RT and the reaction is stirred for 2 h at RT. It is diluted with water, the organic phase is washed with water and dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, DCM/MeOH 9:1). The oily residue is triturated with diisopropylether, filtered off from the insoluble residue and the filtrate is evaporated to dryness i.vac.

Workup

  1. washthe organic phase is washed with water
  2. dry with materialdried over MgSO4
  3. customis purified by chromatography (silica gel, DCM/MeOH 9:1)
  4. customThe oily residue is triturated with diisopropylether
  5. filtrationfiltered off from the insoluble residue
  6. customthe filtrate is evaporated to dryness i.vac

Sources & evidence

ORD record
ord-b6261c3176534e5a80a1fbba7fc85fc7
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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