2-Pyrrolidone → HCID 847897, compound

HRID 1883348Notes

Reaction equation

HRID 1883348 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.I[C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[O:31]>[Cu]I.O1CCOCC1>[CH3:24][C:22]1[CH:23]=[C:18]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:19]=[C:20]([CH3:25])[CH:21]=1

Participants

7

Reactant 4

HCID 120252-PyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 847897HCID 847897, compoundYield 98.1%

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

An oven-dried resealable Schlenk tube was charged with CuI (2.0 mg, 0.0105 mmol, 1.0 mol %), K3PO4 (450 mg, 2.12 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (13 μL, 0.108 mmol, 10 mol %), 5-iodo-m-xylene (150 AL, 1.04 mmol), 2-pyrrolidinone (94 μL, 1.24 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting pale yellow suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:2; 20 mL fractions). Fractions 12-23 provided 193 mg (98% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 7.23 (s, 2H), 6.82 (s, 1H), 3.85 (t, J=7.1 Hz, 2H), 2.61 (t, J=8.1 Hz, 2H), 2.34 (s, 6H), 2.16 (tt, J=8.1, 7.1 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 174.1, 139.2, 138.4, 126.3, 118.0, 49.1, 32.8, 21.5, 18.1. IR (neat, cm−1): 1692, 1596, 1480, 1393, 1333, 1247, 852. Anal. Calcd for C12H15NO: C, 76.16; H, 7.99. Found: C, 76.06; 8.06.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting pale yellow suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:2; 20 mL fractions)

Sources & evidence

ORD record
ord-26b8ae9a5dc24db6a1444783e5851b44
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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