1,2-Diaminocyclohexane, trans- → HCID 20740832, compound

HRID 2179162Notes

Reaction equation

HRID 2179162 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H:9]1([NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:15].I[C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1>[Cu]I.COCCOCCOC>[CH3:24][C:22]1[CH:23]=[C:18]([N:15]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]2[NH2:16])[CH:19]=[C:20]([CH3:25])[CH:21]=1

Participants

6

Reactant 3

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

Product 1

HCID 20740832HCID 20740832, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8150DiglymeSolvent

Conditions

Temperature
140 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (40 mg, 0.210 mmol), K3PO4 (1.30 g, 6.12 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (240 μL, 2.00 mmol), 5-iodo-m-xylene (900 μL, 6.24 mmol) and 2-methoxyethyl ether (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 140° C. for 24 h. The resulting dark brown 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; chloroform-chloroform saturated with aq NH3-methanol 40:40:1; 15 mL fractions). Fractions 7-14 provided 465 mg (72% yield) of the product as a tan solid. 1H NMR (400 MHz, CDCl3): δ 6.67 (s, 1H), 6.57 (s, 2H), 3.65-3.55 (m, 1H), 2.68-2.58 (m, 1H), 2.28 (s, 12H), 2.08-1.92 (m, 2H), 1.83-1.64 (m, 2H), 1.58-1.10 (m, 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 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; chloroform-chloroform saturated with aq NH3-methanol 40:40:1; 15 mL fractions)

Sources & evidence

ORD record
ord-c72895f0d2614b849e78eab1b9fdecbc
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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