1,2-Diaminocyclohexane, (+)- → HCID 86686002, compound

HRID 2277709Notes

Reaction equation

HRID 2277709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH:5]2[CH2:12][CH3:13].Br[C:15]1[C:24]2[CH2:23][CH2:22][CH2:21][CH:20]([NH2:25])[C:19]=2[CH:18]=[N:17][CH:16]=1.[C@H]1(N)CCCC[C@@H]1N>O1CCOCC1.[Cu]I>[NH2:25][CH:20]1[C:19]2[CH:18]=[N:17][CH:16]=[C:15]([N:6]3[CH:5]([CH2:12][CH3:13])[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[C:7]3=[O:11])[C:24]=2[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 4793071,2-Diaminocyclohexane, (+)-HCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amineHCID 84733318HCID 84733318, compound

Product 1

HCID 86686002HCID 86686002, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-chloro-3-ethyl-2,3-dihydro-isoindol-1-one (intermediate A-13-1, 390 mg, 2 mmol), 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate B-12[A], 339 mg, 1.5 mmol), CuI (38 mg, 0.2 mmol), (1S,2S)-cyclohexane-1,2-diamine (45 mg, 0.4 mmol) and CsCO3 (750 mg, 4 mmol) were dissolved in dioxane (10 mL) and heated at 140° C. for 12 hours. After cooling to room temperature, the reaction mixture was filtered through a pad of silica gel (0.5-1 cm) and rinsed with diethyl ether. The combined filtrate was concentrated in vacuo to afford a crude product which was used in the next step reaction without further purification. MS: 342.1 (M+H+)

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a pad of silica gel (0.5-1 cm)
  3. washrinsed with diethyl ether
  4. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-81c2588b271e4a599d46dbb02d519fd6
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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