Dodecane → HCID 11033428, compound

HRID 1242967Notes

Reaction equation

HRID 1242967 reaction equation
CC(C)([O-])C.[Na+].[C@@H]1(N)CCCC[C@H]1N.CCCCCCCCCCCC.I[C:28]1[CH:29]=[C:30]([CH3:35])[CH:31]=[C:32]([CH3:34])[CH:33]=1.[C:36](=[NH:49])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>[Cu]I.O1CCOCC1>[CH3:34][C:32]1[CH:33]=[C:28]([N:49]=[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:29]=[C:30]([CH3:35])[CH:31]=1

Participants

8

Reactant 5

HCID 8182DodecaneHCID 438061,2-Diaminocyclohexane, trans-HCID 136809Benzophenone imineHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 11033428HCID 11033428, compoundYield 15.5%

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 %), sodium tert-butoxide (150 mg, 1.56 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (13 μL, 0.108 mmol, 11 mol %), dodecane (235 μL), 5-iodo-m-xylene (150 μL, 1.04 mmol), benzophenone imine (210 μL, 1.25 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 36 h. The resulting dark brown 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 (2×15 cm; hexane-ethyl acetate 30:1; 15 mL fractions). Fractions 6–11 provided 46 mg (15% yield) of the product as a pale tan solid. 1H NMR (300 MHz, CDCl3): δ 7.79–7.75 (m, 2H), 7.52–7.40 (m, 3H), 7.34–7.26 (m, 3H), 7.20–7.15 (m, 2H), 6.60 (s, 1H), 6.39 (s, 2H) 2.19 (s, 6H).

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting dark brown 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 (2×15 cm; hexane-ethyl acetate 30:1; 15 mL fractions)

Sources & evidence

ORD record
ord-f5d8d1358db34814a64c007d168e7b36
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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