2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 18430946, compound

HRID 1278626Notes

Reaction equation

HRID 1278626 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([C:21](O)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=CC2C(=CC=CC=2)[N:28]1C(OCC)=O)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([C:21]([NH2:28])=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 516892Sodium BicarbonateHCID 18430908HCID 18430908, compound

Product 1

HCID 18430946HCID 18430946, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-[2-(4-benzyl-1-piperazinyl)ethyl]cyclopentanecarboxylic acid (300 mg, 0.948 mmol), NH4HCO3 and 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (469 mg, 3.49 mmol) in chloroform (5.0 ml) was stirred for 2 d. To the mixture was added sat NaHCO3 (3 ml) and the mixture was extracted with dichloromethane After the solvent was removed in vacuo, the residue was extracted with dichloromethane (30 ml). The extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo . The residue was purified by column chromatography (SiO2, 200-350 mesh/21 g/dichloromethane:methanol=97:3) to provide a yellow oil (174 mg/58%).

Workup

  1. additionTo the mixture was added
  2. extractionthe mixture was extracted with dichloromethane After the solvent
  3. customwas removed in vacuo
  4. extractionthe residue was extracted with dichloromethane (30 ml)
  5. washThe extract was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/21 g/dichloromethane:methanol=97:3)
  10. customto provide a yellow oil (174 mg/58%)

Sources & evidence

ORD record
ord-390e6a38a6aa4448a7b8e4d35fcf23e8
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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