1-(2-Hydroxyethyl)piperazine → HCID 58981797, compound

HRID 1182602Notes

Reaction equation

HRID 1182602 reaction equation
CCN=C=NCCCN(C)C.Cl.[OH:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[C:22]1([CH:28]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:29][CH2:30][O:31][C:32]([C:34]2[CH:39]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=3)[C:38]([C:47](O)=[O:48])=[C:37]([CH3:50])[NH:36][C:35]=2[CH3:51])=[O:33])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:22]1([CH:28]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:29][CH2:30][O:31][C:32](=[O:33])[C:34]2[C:39]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=3)=[C:38]([C:47]([N:19]3[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][OH:13])[CH2:17][CH2:18]3)=[O:48])[C:37]([CH3:50])=[N:36][C:35]=2[CH3:51])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9827369HCID 9827369, compound

Product 1

HCID 58981797HCID 58981797, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

118 mg (0.620 mmol) of WSC hydrochloride and 80 mg (0.610 mmol) of 1-(2-hydroxyethyl) piperazine in the ice bath were added to 252 mg (0.510 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid mono (3,3-diphenylpropyl) ester in 8 ml of dichloromethane and stirred at room temperature overnight. 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 dissolved in 8 ml of dichloromethane. 4 ml of trifluoroacetic acid was added in the ice bath and stirred at room temperature for 9 hours. The reaction mixture was concentrated under reduced pressure, followed by basifying with 1N NaOH aq. After extracting it with ethyl acetate, The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (chloroform/methanol=1000/1) to obtain the title compound.

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. dissolutionThe residue was dissolved in 8 ml of dichloromethane
  5. addition4 ml of trifluoroacetic acid was added in the ice bath
  6. stirringstirred at room temperature for 9 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. extractionAfter extracting it with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by the basic silica gel chromatography (chloroform/methanol=1000/1)

Sources & evidence

ORD record
ord-0f7a9eaf83914c5f8cbf2fb0bf1d7304
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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