Potassium Carbonate → HCID 20740830, compound

HRID 2179161Notes

Reaction equation

HRID 2179161 reaction equation
C([O-])([O-])=O.[K+].[K+].[C@@H:7]1([NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH2:13].I[C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1>[Cu]I>[CH3:23][C:18]1[CH:17]=[C:16]([NH:13][C@@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]2[NH2:14])[CH:21]=[C:20]([CH3:22])[CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 20740830HCID 20740830, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (40 mg, 0.210 mmol), K2CO3 (850 mg, 6.15 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (240 μL, 2.00 mmol) and 5-iodo-m-xylene (900 μL, 6.24 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 100° C. for 23 h. The resulting purple-blue suspension was cooled to room temperature and filtered through a 2×1 cm pad of Celite eluting with 50 mL of dichloromethane. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane saturated with aq NH3-methanol 40:1; 15 mL fractions). Fractions 9-13 provided 178 mg (41% yield) of the product as a tan solid. 1H NMR (400 MHz, CDCl3): δ 6.39 (s, 1H), 6.34 (s, 2H), 3.36 (br s, 1H), 3.03-2.92 (m, 1H), 2.56-2.46 (m, 1H), 2.25 (s, 6H), 2.20-2.10 (m, 1H), 2.08-1.95 (m, 1H), 1.83-1.70 (n, 2H), 1.55-1.20 (m, 5H), 1.10-1.00 (m, 1H).

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting purple-blue suspension was cooled to room temperature
  4. filtrationfiltered through a 2×1 cm pad of Celite
  5. washeluting with 50 mL of dichloromethane
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane saturated with aq NH3-methanol 40:1; 15 mL fractions)

Sources & evidence

ORD record
ord-86852b09bff84e9e9db520f977a6a9b7
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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