1-Methylpiperazine → HCID 10226218, compound

HRID 1727926Notes

Reaction equation

HRID 1727926 reaction equation
CCN=C=NCCCN(C)C.Cl.CN1CCNCC1.[C:20]1([CH:26]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:27][CH2:28][O:29][C:30]([C:32]2[C:33]([CH3:49])=[N:34][C:35]([CH3:48])=[C:36](C(O)=O)[C:37]=2[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)=[O:31])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:20]1([CH:26]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:27][CH2:28][O:29][C:30](=[O:31])[C:32]2[C:37]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=3)=[CH:36][C:35]([CH3:48])=[N:34][C:33]=2[CH3:49])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10117784HCID 10117784, compound

Product 1

HCID 10226218HCID 10226218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

447 mg (2.33 mmol) of WSC hydrochloride and 0.254 ml (2.29 mmol) of N-methylpiperazine in the ice bath were added to 952 mg (1.90 mmol) of 4-(3-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid mono (3,3-diphenylpropyl) ester in 40 ml of dichloromethane and stirred at room temperature for 2 nights. Saturated aqueous sodium hydrogencarbonate solution was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1) to obtain the title compound as a by-product.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-4dc63b4355784a55b622ef6b8633a3b5
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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