Triethylamine → HCID 15572888, compound

HRID 1154942Notes

Reaction equation

HRID 1154942 reaction equation
[C:1]([CH2:4][CH:5]([CH3:19])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:18])[NH:13]2)([OH:3])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH2:33]([NH:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[CH3:34]>O.C(OCC)(=O)C>[CH:36]1([N:35]([CH2:33][CH3:34])[C:1]([CH2:4][CH:5]([CH3:19])[CH2:6][O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][C:12](=[O:18])[NH:13]3)=[O:3])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21609N-Ethyl cyclohexylamineHCID 12819304HCID 12819304, compound

Product 1

HCID 15572888HCID 15572888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.6 Grams of 5-(3-carboxy-2-methylpropoxy)-3,4-dihydrocarbostyril and 1.6 ml of triethylamine are added to 200 ml of ethyl acetate, followed by dropwise addition of 1.0 ml of ethyl chloroformate under external ice cooling and agitation while maintaining the internal temperature at 10° to 20° C. Thereafter, the mixture is agitated at room temperature for 1 hour, added with 1.4 g of N-ethylcyclohexylamine and further agitated for 1.5 hours. The reaction solution is poured into water to separate the liquid, and the organic layer is washed with dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order and then dried with anhydrous Na2SO4. After filtering off the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from ligroin-benzene, obtaining 1.5 g of 5-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-2-methylpropoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 114°-115.5° C.

Workup

  1. temperatureagitation while maintaining the internal temperature at 10° to 20° C
  2. stirringfurther agitated for 1.5 hours
  3. customto separate the liquid
  4. washthe organic layer is washed with dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationAfter filtering off the inorganic matter
  7. concentrationthe mother liquor is concentrated
  8. customthe residue is recrystallized from ligroin-benzene

Sources & evidence

ORD record
ord-3b0fcf2a24244c7281bfb159ecf29a86
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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