1,2-Diaminocyclohexane, trans- → HCID 11277903, compound

HRID 1883352Notes

Reaction equation

HRID 1883352 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.I[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1>[Cu]I.O1CCOCC1>[C:1]([O:5][C:6]([N:8]([C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 137930t-Butyl carbanilateHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 11277903HCID 11277903, compoundYield 97%

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 %), N-tert-butoxycarbonylaniline (200 mg, 1.04 mmol), 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 (190 μL, 1.32 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred magnetically at 110° C. for 23 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 20:1; 20 mL fractions). Fractions 12-20 provided 299 mg (97% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 7.36−7.30 (m, 2H), 7.27−7.16 (m, 3H), 6.87 (s, 2H), 6.85 (s, 1H), 2.30 (s, 6H), 1.48 (s, 9H). 13C NMR (100 MHz, CDCl3): δ 153.9, 143.2, 142.7, 138.3, 128.6, 127.5, 126.9, 125.4, 124.8, 80.9, 28.2, 21.2. Anal. Calcd for C19H23NO2: C, 76.74; H, 7.79. Found: C, 76.61; 7.87.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  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 20:1; 20 mL fractions)

Sources & evidence

ORD record
ord-ae39ee0a9f1a4fc7a5128276cb20f919
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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