1-Methylpiperazine → HCID 10226218, compound

HRID 1182604Notes

Reaction equation

HRID 1182604 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-286114b9226649ee91f42d8b9482d18a
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

Loading…