Toluene → HCID 58235963, compound

HRID 1193357Notes

Reaction equation

HRID 1193357 reaction equation
Cl.Cl.Cl.[CH3:4][N:5]1[CH2:10][CH2:9][N:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH2:17])[CH2:12]2)[CH2:7][CH2:6]1.[C:18]([O-:21])([O-])=[O:19].[K+].[K+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:30]([O:21][C:18](=[O:19])[NH:17][C@H:13]1[CH2:14][CH2:15][CH2:16][C@@H:11]([N:8]2[CH2:7][CH2:6][N:5]([CH3:4])[CH2:10][CH2:9]2)[CH2:12]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66607290HCID 66607290, compound

Product 1

HCID 58235963HCID 58235963, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(cis)-3-(4-Methylpiperazin-1-yl)cyclohexanamine trihydrochloride (5.0 g, 16.39 mmol, 1.0 eq.) and K2CO3 (9.05 g, 65.56 mmol, 4.0 eq.) were dissolved in water (15 ml); a solution of Cbz-C1 (2.85 g, 16.39 mmol, 1.0 eq.) in toluene (25 ml) was added at 0° C., and the reaction mixture was then stirred for 16 hours at RT. The reaction solution was diluted with water (15 ml) and the phases were separated. The org. phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (Alox, 1% MeOH in DCM). Yield: 37% (2.0 g, 6.04 mmol)

Workup

  1. customthe phases were separated
  2. dry with materialphase was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (Alox, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-24e31044b97943a888e0a1b5562844fd
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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