Benzaldehyde → Methyl 2-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1967991Notes

Reaction equation

HRID 1967991 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1CO[C:6]2=O.C1([C:15](N2CCN(C(C3C=CC(C=O)=CC=3)=O)CC2)=[O:16])CC1.[O-]S([O-])(=O)=O.[Mg+2].[CH:39]1([C:42]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([C:52]3[CH:69]=[CH:68][C:55](/[CH:56]=[N:57]/[C:58]4[CH:66]=[CH:65][CH:64]=[C:63]5[C:59]=4[CH2:60][O:61][C:62]5=[O:67])=[CH:54][CH:53]=3)=[O:51])[CH2:46][CH2:45]2)=[O:43])[CH2:41][CH2:40]1.C(=O)C1C=CC=CC=1.C[O-].[Na+].C(OCC)(=O)CC>ClCCl>[CH:39]1([C:42]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([C:52]3[CH:69]=[CH:68][C:55]([CH:56]4[CH:6]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=5)[C:60](=[O:61])[C:59]5[C:63]([C:62]([O:16][CH3:15])=[O:67])=[CH:64][CH:65]=[CH:66][C:58]=5[NH:57]4)=[CH:54][CH:53]=3)=[O:51])[CH2:46][CH2:45]2)=[O:43])[CH2:41][CH2:40]1

Participants

9

Reactant 7

HCID 240BenzaldehydeHCID 7749Ethyl PropionateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10942334Sodium MethoxideHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 866390294-(4-(Cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehydeHCID 178519075HCID 178519075, compound

Product 1

HCID 67260447Methyl 2-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Aminoisobenzofuran-1(3H)-one (372.5 mg, 2.5 mmol), 4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzaldehyde (645 mg, 2.5 mmol) and 1 g of MgSO4 were added into 40 mL of dichloromethane and stirred under reflux overnight, then the mixture was evaporated under reduced pressure and the residues was dried in vacuum. 385 mg of (E)-4-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzylideneamino)isobenzofuran-1 (3H)-one. A mixture of (E)-4-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzylideneamino)isobenzofuran-1(3H)-one (385 mg, 0.92 mmol), benzaldehyde (97.9 mg, 0.97 mmol), sodium methanolate (199 mg, 3.68 mmol) and ethyl propionate (10 mL) was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1 to 5:1) to give 300 mg of methyl 2-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate. LC-MS (ESI) m/z: 538 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. customthe mixture was evaporated under reduced pressure
  3. customthe residues was dried in vacuum
  4. stirringwas stirred at room temperature overnight
  5. customThen the resulting mixture was evaporated under reduced pressure
  6. extractionextracted with ethyl acetate (100 mL×4)
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1 to 5:1)

Sources & evidence

ORD record
ord-99caa0731a734a34b4dda30a8c0c2011
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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