O-Phenylenediamine → HCID 68671013, compound

HRID 2047365Notes

Reaction equation

HRID 2047365 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.O.O[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=N1.C1(N)C=CC=CC=1N>CN(C=O)C.CN(C)C1C=CN=CC=1>[NH2:36][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[NH:38][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)[CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 686700692-Chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acid

Product 1

HCID 68671013HCID 68671013, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acid (0.40 g, 1.29 mmol) in dry DMF (5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.25 g, 1.29 mmol), followed by 1-hydroxybenzotriazole hydrate (1-HOBt) (0.11 g, 0.77 mmol) and dimethyl-pyridin-4-yl-amine (DMAP) (0.08 g, 0.64 mmol). After 3 h stirring at room temperature, 1,2-phenylenediamine (0.21 g, 1.93 mmol) was added, and the resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure, then diluted with dichlomethane (20 mL) and washed with saturated Na2CO3 solution (2×5 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting solid was purified by flash chromatography (eluent:dichloromethane:MeOH:NH3 in MeOH (2M)/9:0.5:0.5) to obtain 0.18 g (35%) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe solution was evaporated under reduced pressure
  3. additiondiluted with dichlomethane (20 mL)
  4. washwashed with saturated Na2CO3 solution (2×5 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting solid was purified by flash chromatography (eluent:dichloromethane:MeOH:NH3 in MeOH (2M)/9:0.5:0.5)

Sources & evidence

ORD record
ord-5cc06559e25b4b6698c946b450a9a111
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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