Water → HCID 19030751, compound

HRID 266794Notes

Reaction equation

HRID 266794 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 re-crystallized 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 re-crystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-b296e56244604d5fb8a85a19456e904f
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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