Triethylamine → HCID 15572888, compound

HRID 1154940Notes

Reaction equation

HRID 1154940 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(C)C)=O.[CH2:35]([NH:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[CH3:36]>CN(C=O)C>[CH:38]1([N:37]([CH2:35][CH3:36])[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])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 12819304HCID 12819304, compound

Product 1

HCID 15572888HCID 15572888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 Grams of 5-(3-carboxy-2-methylpropoxy)-3,4-dihydrocarbostyril and 0.8 ml of triethylamine are added to 50 ml of DMF, and the mixture is added dropwise with 0.65 ml of isobutyl chloroformate under external ice cooling and agitation at internal temperature of 0° to 10° C. After this dropwise addition, the mixture is agitated at room temperature for 30 minutes, added dropwise with 0.7 g of N-ethylcyclohexylamine and further agitated at room temperature for 2 hours. The solvent is distilled off and the residue is dissolved in 200 ml of chloroform, washed with diluted hydrochloric acid, aqueous K2CO3 solution 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 to obtain 0.8 g of 5-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-2-methylpropoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. m.p. 114°-115.5° C.

Workup

  1. customat internal temperature of 0° to 10° C
  2. additionAfter this dropwise addition
  3. stirringfurther agitated at room temperature for 2 hours
  4. distillationThe solvent is distilled off
  5. dissolutionthe residue is dissolved in 200 ml of chloroform
  6. washwashed with diluted hydrochloric acid, aqueous K2CO3 solution and water in that order
  7. dry with materialdried with anhydrous Na2SO4
  8. filtrationAfter filtering off the inorganic matter
  9. concentrationthe mother liquor is concentrated
  10. customthe residue is recrystallized from ligroin-benzene

Sources & evidence

ORD record
ord-dfe2e964ab8e4e919eed9500248c1a6a
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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