Triphenylphosphine → 4-((4-Chloro-2-iodophenoxy)methyl)-1-methylpiperidine

HRID 1882250Notes

Reaction equation

HRID 1882250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17]O)[CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2719711-Methyl-4-piperidinemethanolHCID 6202344-Chloro-2-iodophenol

Product 1

HCID 588801664-((4-Chloro-2-iodophenoxy)methyl)-1-methylpiperidineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-chloro-2-iodophenol (1.72 g, 6.75 mmol) in anhydrous THF (10.0 mL) were sequentially added (1-methylpiperidin-4-yl)methanol (1.31 g, 10.14 mmol) and triphenyl phosphine (2.66 g, 10.14 mmoL). The reaction mixture was cooled to 0° C., and to it diisopropyl-azodicarboxylate (1.96 mL, 10.14 mmol) was added in drop wise manner. After the addition was over, stirring continued for another 0.5 h at 0° C. and then for 12 h at room temperature. Solvents were removed in vacuum and the residue was purified by silica gel column chromatography, providing Compound 173 (1.85 g, 75%).

Workup

  1. additionAfter the addition
  2. waitfor 12 h at room temperature
  3. customSolvents were removed in vacuum
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8bc36d71bd044087a18fd16e66030a89
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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