Iodobenzene → N-BOC-4-(phenylethynyl)piperidine

HRID 605808Notes

Reaction equation

HRID 605808 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[CH:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.[Cu](I)I>[C:17]1([C:2]#[C:1][CH:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 11575IodobenzeneHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Product 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidineYield 90.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 4-ethynylpiperidine-1-carboxylate (12.5 g) and iodobenzene (12.8 g) was dissolved in THF:TEA=1:1 (v/v) mixed solvent (125 ml), then at room temperature, copper iodide (455 mg) and palladium tetrakistriphenylphosphine complex (1.38 g) were added thereto in that order, followed by stirring overnight at room temperature. The solvent was evaporated, EtOAc was added to it, and washed with aqueous 1 M hydrochloric acid solution, water and saturated brine in that order. This was dried over magnesium sulfate, and the solvent was evaporated to obtain a light brown oil. This was purified by silica gel column chromatography (eluent: hexane:EtOAc=19:1 (v/v)) to obtain tert-butyl 4-(phenylethynyl)piperidine-1-carboxylate (15.5 g) as a light brown oil.

Workup

  1. customThe solvent was evaporated
  2. additionEtOAc was added to it
  3. washwashed with aqueous 1 M hydrochloric acid solution, water and saturated brine in that order
  4. dry with materialThis was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customto obtain a light brown oil
  7. customThis was purified by silica gel column chromatography (eluent: hexane:EtOAc=19:1 (v/v))

Sources & evidence

ORD record
ord-7594c6b3670548099df7075756b0f7c0
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

Loading…