Water → HCID 19030751, compound

HRID 483502Notes

Reaction equation

HRID 483502 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:8]2=[O:9])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:25](Cl)(=[O:29])[O:26][CH2:27][CH3:28].O>ClCCl>[CH2:27]([O:26][C:25]([N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:8]2=[O:9])[CH2:3][CH2:2]1)=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 107281851-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 19030751HCID 19030751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Piperidinyl)-3,4-dihydrocarbostyril (500 mg) and triethylamine (0.6 ml) are dissolved in dichloromethane (10 ml) and thereto is added dropwise ethyl chlorocarbonate (0.31 ml) gradually. The mixture is stirred at room temperature for 2 hours and poured into water. The mixture is extracted with chloroform, dried with sodium carbonate and purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1). The resultant is recrystallized from ethanol/n-hexane- to give 1-(1-ethoxycarbonyl-4-piperidinyl)-3,4-dihydrocarbostyril (0.1 g) as white powder, m.p. 82°-83° C.

Workup

  1. extractionThe mixture is extracted with chloroform
  2. dry with materialdried with sodium carbonate
  3. custompurified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1)
  4. customThe resultant is recrystallized from ethanol/n-hexane-

Sources & evidence

ORD record
ord-164ebae11a60444fbb44da7542878aff
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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