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

HRID 2074314Notes

Reaction equation

HRID 2074314 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-1667f80477fa4cb380236c04e925799a
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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