1-Phenylpiperazine → 2-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(4-phenylpiperazine-1-carbonyl)-1,4-dihydropyridine-3-carboxylate

HRID 1700357Notes

Reaction equation

HRID 1700357 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O-:16])=O)=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.[C:38]1([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([N:47]3[CH2:48][CH2:49][N:44]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:45][CH2:46]3)=[O:16])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757801Mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 183183122-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(4-phenylpiperazine-1-carbonyl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

216 mg (0.60 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 147 mg (0.76 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.14 ml (0.92 mmol) of 1-phenylpiperazine and 25 mg (0.20 mmol) of 4-dimethylaminopyridine were stirred in 10 ml of dichloromethane at room temperature for 4 days. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After the extraction 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 (chloroform/methanol=100/1) to obtain the title compound

Workup

  1. extractionAfter the extraction 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 (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-cdefbc0ece06463baa56f24fdd466b49
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

Loading…