Water → HCID 19031029, compound

HRID 1708269Notes

Reaction equation

HRID 1708269 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:18])[N:9]2[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].C(N(CC)CC)C.O>ClCCl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:18])[N:9]2[CH:12]2[CH2:13][CH2:14][N:15]([C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[CH:29][C:21]=3[O:20][CH3:19])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 180010904-Ethoxy-2-methoxybenzoic acidHCID 18960739HCID 18960739, compound

Product 1

HCID 19031029HCID 19031029, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Fluoro-1-(4-piperidinyl)-3,4-dihydrocarbostyril (2.37 g), 2-methoxy-4-ethoxybenzoic acid (2.43 g) and bis(2-oxo-oxazolydinyl)phosphinyl chloride (3.65 g) are dissolved in dichloromethane (50 ml) and thereto is added dropwise triethylamine (4 ml). The mixture is stirred at room temperature overnight and poured into water. The mixture is extracted with dichloromethane, dried with sodium carbonate and then purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:1). The resultant is recrystallized from ethanol/water to give 7-fluoro-1-[1-(2-methoxy-4-ethoxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (2.5 g) as white powder, m.p. 159°-161° C.

Workup

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

Sources & evidence

ORD record
ord-9bb28b7119aa4c2e921aaafc782c87da
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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