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Triethylamine → 1-[1-(2-Pyrrolylcarbonyl)-4-piperidinyl]-3,4-dihydrocarbostyril

HRID 483503
Notes
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Reaction equation

HRID 483503 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.[NH:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](O)=[O:31].P(C#N)(OCC)(OCC)=O>ClCCl.O>[NH:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]([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:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12473Pyrrole-2-Carboxylic AcidHCID 76257Diethyl cyanophosphonateHCID 107281851-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 189607501-[1-(2-Pyrrolylcarbonyl)-4-piperidinyl]-3,4-dihydrocarbostyrilYield 28.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

1-(4-Piperidinyl)-3,4-dihydrocarbostyril (500 mg), triethylamine (1.2 ml) and pyrrole-2-carboxylic acid (314 mg) are dissolved in dichloromethane (10 ml) and thereto is added dropwise diethyl cyanophosphate (0.82 ml) under ice cooling. The mixture is stirred with ice cooling for 1 hour and then stirred at room temperature for 2 hours. The mixture is poured into water, extracted with chlorform, dried with sodium carbonate and purified by silica gel column chromatography (solvent; dichloromethane:methanol=20:1). The resultant is recrystallized from n-hexane/diethyl ether to give 1-[1-(2-pyrrolylcarbonyl)-4-piperidinyl]-3,4-dihyrocarbostyril (0.2 g), as white powder, m.p. 161°-162° C. (decomposed).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionextracted with chlorform
  3. dry with materialdried with sodium carbonate
  4. custompurified by silica gel column chromatography (solvent; dichloromethane:methanol=20:1)
  5. customThe resultant is recrystallized from n-hexane/diethyl ether

Sources & evidence

ORD record
ord-3df7eef01b584420b8478d9bcdf19a24
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05225402

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes