Ethylenediamine → HCID 50940452, compound

HRID 529470Notes

Reaction equation

HRID 529470 reaction equation
[O:1]=[C:2]1[C@@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4][NH:3]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N)CN>[Cu]I.O1CCOCC1>[O:1]=[C:2]1[C@@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:6][CH2:5][CH2:4][N:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 1247873-tert-Butyloxycarbonylamino-2-piperidone

Product 1

HCID 50940452HCID 50940452, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a sealed-vial was added (S)-tert-butyl 2-oxopiperidin-3-ylcarbamate (162 mg, 0.756 mmol), potassium phosphate (321 mg, 1.51 mmol), iodobenzene (0.101 mL, 0.907 mmol), ethylenediamine (0.020 mL, 0.30 mmol), dioxane (3 mL) and molecular sieves followed by copper(I) iodide (57.6 mg, 0.302 mmol). The vial was purged with nitrogen gas and sealed. Then the reaction was stirred at 110° C. for 40 hr. The reaction was diluted with EtOAc (30 mL) and washed with water (20 mL) and saturated aqueous NaCl (20 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified by RP prep-HPLC (Method A) to give (S)-tert-butyl 2-oxo-1-phenylpiperidin-3-ylcarbamate (100 mg, 0.344 mmol, 45.6% yield) as a white solid. Anal. Calcd. for C16H22N2O3 m/z 290.3. found: 291.2 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.40 (t, J=7.70 Hz, 2H), 7.33-7.20 (m, 3H), 5.56 (br. s., 1H), 4.37-4.20 (m, 1H), 3.78-3.66 (m, 2H), 2.63 (dd, J=12.37, 5.77 Hz, 1H), 2.16-1.97 (m, 2H), 1.81-1.661 (m, 1H), 1.47 (s, 9H).

Workup

  1. customThe vial was purged with nitrogen gas
  2. customsealed
  3. additionThe reaction was diluted with EtOAc (30 mL)
  4. washwashed with water (20 mL) and saturated aqueous NaCl (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by RP prep-HPLC (Method A)

Sources & evidence

ORD record
ord-32b5d818eb714fcd91fead9205fdd448
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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