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

HRID 1157173Notes

Reaction equation

HRID 1157173 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[CH:22])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Product 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidineYield 25.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Iodobenzene (135 μl, 1.2 mmols), 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (209 mg, 1 mmols) and triethylamine (167 μl, 1.2 mmols) were dissolved in acetonitrile (6 ml). Dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmols) and Cul (10 mg, 0.05 mmols) were added, and reaction mixture was stirred at room temperature overnight and continued to stir at 50 C. for two more hours before partitioning between ethyl acetate and water. Organic layer was isolated, washed with 1 N HCl, brine and dried (MgSO4). Solvents were removed and residue was purified by column chromatography on silica gel using solutions of ethyl acetate in hexanes (1:4; 1:2) to yield the title compound (74 mg). LCMS m/e (230, M−t-Bu+2H)

Workup

  1. customreaction mixture
  2. stirringto stir at 50 C
  3. customfor two more hours before partitioning between ethyl acetate and water
  4. customOrganic layer was isolated
  5. washwashed with 1 N HCl, brine
  6. dry with materialdried (MgSO4)
  7. customSolvents were removed
  8. customresidue was purified by column chromatography on silica gel using solutions of ethyl acetate in hexanes (1:4; 1:2)

Sources & evidence

ORD record
ord-fcb2bd50885246cd8226fd60faee832b
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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