Potassium Hydroxide → HCID 379996, compound

HRID 1588252Notes

Reaction equation

HRID 1588252 reaction equation
[OH-:1].[K+].[CH2:3]([N:10]1[CH2:33][CH2:32][C:13]2([N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16](=[O:24])[NH:15][C:14]2=NC2CCCCC2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)CO>[CH2:3]([N:10]1[CH2:11][CH2:12][C:13]2([N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16](=[O:24])[NH:15][C:14]2=[O:1])[CH2:32][CH2:33]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 135492826HCID 135492826, compound

Product 1

HCID 379996HCID 379996, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
50 °C

Procedure

Potassium hydroxide (50.4 g, 0.9 mol) was added to 300 mL of ethylene glycol followed by 8-benzyl-4-cyclohexylimino-1-phenyl-1,3,8-triazaspiro[4,5]decane-2-one (37.7 g, 0.11 mol) from Step A. The reaction mixture was heated slowly to a gentle reflux and 100 mL of solvent was removed by distillation over a 4.5 hour period. The reaction mixture was then cooled in ice to 50° C. and poured into water (500 mL). The aqueous solution was adjusted to approximately pH 8-9 by adding concentrated hydrochloric acid while cooling in ice. The precipitate was filtered and washed with water to give 25.8 g of solid. The solid was crystallized from boiling chloroform to give 19.45 g of the title compound, m.p. 159°-160° C.

Workup

  1. temperatureThe reaction mixture was heated slowly to
  2. temperaturea gentle reflux
  3. custom100 mL of solvent was removed by distillation over a 4.5 hour period
  4. additionpoured into water (500 mL)
  5. additionby adding concentrated hydrochloric acid
  6. temperaturewhile cooling in ice
  7. filtrationThe precipitate was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-c078125f915a4674ae1a6628f6b46f08
Source dataset
uspto-grants-1993_06
Patent number
US05221675

Reaction notes

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