Triethylamine → Hydrocarbostyril

HRID 1460685Notes

Reaction equation

HRID 1460685 reaction equation
C([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)(O)=O.CNC1CCN(CC2C=CC=CC=2)CC1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O>[NH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 64796Hydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3 Grams of 6-carboxy-3,4-dihydrocarbostyril and 3.5 g of 4-methylamino-1-benzylpiperidine were dispersed in 40 ml of dimethylformamide, to this dispersion was added dropwise, under ice-cooled condition, 2.61 ml of diethyl cyanophosphate and 2.39 ml of triethylamine in 10 ml of dimethylformamide solution. The reaction mixture was stirred under ice-cooled condition for 1 hour, further stirred at room temperature for 2 hours, then the reaction mixture was poured into ice-water. Said mixture was extracted with chloroform, then extract was dried with anhydrous sodium carbonate, then the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography, and recrystallized from acetonitrile to yield 3 g of [N-methyl-N-(1-benzyl-4-piperidyl)amino]carbonyl]-3,4-dihydrocarbostyril.1/2-hydrate. White powdery substance. Melting point: 186° C.-188° C. (decomp.)

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooled condition for 1 hour
  3. stirringfurther stirred at room temperature for 2 hours
  4. extractionwas extracted with chloroform
  5. extractionextract
  6. dry with materialwas dried with anhydrous sodium carbonate
  7. customthe solvent was removed by evaporation
  8. customThe residue thus obtained
  9. customwas purified by means of a silica gel column chromatography
  10. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-85ea005a5fdc4fb98e179cebfff0318f
Source dataset
uspto-grants-1991_12
Patent number
US05071856

Reaction notes

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