Isopropanol → HCID 20468115, compound

HRID 1903199Notes

Reaction equation

HRID 1903199 reaction equation
C([OH:4])(C)C.[CH2:5]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10])[CH:6]=[CH2:7].C1CCN2C(=NCCC2)CC1.[CH:31]1([N:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH:45](Br)[CH3:46])[CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CO.C(Cl)(Cl)Cl>[CH2:5]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:46][CH2:45][CH2:44][C:43]([N:40]3[CH2:41][CH2:42][N:37]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:38][CH2:39]3)=[O:4])=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10])[CH:6]=[CH2:7]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20468176HCID 20468176, compoundHCID 53721842HCID 53721842, compound

Product 1

HCID 20468115HCID 20468115, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Into 100 ml isopropanol were added 2.0 g of 1-allyl-6-hydroxy-3,4-dihydrocarbostyril and 1.8 ml of DBU. The mixture was refluxed under stirring and 4.2 g of 4-cyclohexyl-1-γ-bromobutylpiperazine was added thereto. After the addition operation, the reaction mixture was further refluxed under stirring for 8 hours, then concentrated. The residue thus obtained was extracted with chloroform and the chloroform layer was washed with 1N-NaOH aqueous solution and water, then dried with anhydrous sodium sulfate. The drying agent was removed by filtration and the mother liquor was concentrated. The residue thus obtained was treated by a silica-gel column chromatography [the solvent used was a mixture of chloroform:methanol=20:1 (vol/vol)]. 3.5 Grams of 1-allyl-6-[3-(4-cyclohexyl-1-piperazinylcarbonyl)propoxy]-3,4-dihydrocarbostyril was obtained as in the form of a colorless syrupy substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureAfter the addition operation, the reaction mixture was further refluxed
  3. stirringunder stirring for 8 hours
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. extractionwas extracted with chloroform
  7. washthe chloroform layer was washed with 1N-NaOH aqueous solution and water
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe mother liquor was concentrated
  11. customThe residue thus obtained
  12. additionwas treated by a silica-gel column chromatography [the solvent

Sources & evidence

ORD record
ord-12518a2a80874aac9e1ebc2ce2cfda99
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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