Triethylamine → HCID 15572887, compound

HRID 1154939Notes

Reaction equation

HRID 1154939 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)([OH:3])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:34]1([CH2:40][NH2:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>O.CN(C)C=O>[CH:34]1([CH2:40][NH:41][C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)=[O:3])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 76688CyclohexanemethylamineHCID 12819271HCID 12819271, compound

Product 1

HCID 15572887HCID 15572887, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.5 Grams of 6-(3-carboxy)propoxy-3,4-dihydrocarbostyril and 1.6 ml of triethylamine are added to 150 ml of dimethylformamide, and the mixture is further added dropwise with 1.3 ml of isobutyl chloroformate under external ice cooling and agitation while maintaining the internal temperature at 10° to 20° C. After this dropwise addition, the mixture is agitated at room temperature for 30 minutes, added with 1.3 ml of cyclohexylmethylamine and further agitated for 1 hour. After the reaction, the reaction solution is poured into about 1 liter of water and the precipitated crystals are filtered out and washed with water. The obtained crystals are dried and recrystallized from chloroform-petroleum ether to obtain 3.0 g of 6-{3-[N-(cyclohexylmethyl)aminocarbonyl]propoxy}-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with m.p. of 170°-172° C.

Workup

  1. temperatureagitation while maintaining the internal temperature at 10° to 20° C
  2. additionAfter this dropwise addition
  3. stirringfurther agitated for 1 hour
  4. customAfter the reaction
  5. filtrationthe precipitated crystals are filtered out
  6. washwashed with water
  7. customThe obtained crystals are dried
  8. customrecrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-85c058f22a7949259d5a3c66e097e323
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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