1-(4-Iodophenyl)piperidine → HCID 19862673, compound

HRID 1165270Notes

Reaction equation

HRID 1165270 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[C:15]#[CH:16]>C(NCC)C.[Cu]I>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:16]#[C:15][CH2:14][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 132036091-(4-Iodophenyl)piperidineHCID 200714346-[(Prop-2-yn-1-yl)oxy]hexan-1-ol

Product 1

HCID 19862673HCID 19862673, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 1-(4-iodophenyl)piperidine (1.5 g), 6-[(2-propynyl)oxy]-1-hexanol (820 mg), BTPC (35 mg) and copper (I) iodide (20 mg) in diethylamine (30 ml) under nitrogen, was stired at room temperature overnight. The solvent was evaporated and the residue was partitioned between EA (50 ml) and 8% aqueous sodium bicarbonate (50 ml). The organic layer was washed with water and brine, dried and concentrated to a dark oil which was purified by FCC eluting with ER to give the title compound as an orange oil (1.2 g), t.l.c. (ER) Rf 0.70.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EA (50 ml) and 8% aqueous sodium bicarbonate (50 ml)
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated to a dark oil which
  6. customwas purified by FCC
  7. washeluting with ER

Sources & evidence

ORD record
ord-a6e996483bdc47e38eddaf8514fe11a6
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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