Isobutyl chloroformate → HCID 20468144, compound

HRID 1903191Notes

Reaction equation

HRID 1903191 reaction equation
[CH2:1]([N:4]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:5]1=[O:6])[CH:2]=[CH2:3].C1CCN2C(=NCCC2)CC1.ClC(OCC(C)C)=O.[CH:41]1([N:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>CO.C(Cl)(Cl)Cl>[CH2:1]([N:4]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][C:19]([N:50]3[CH2:51][CH2:52][N:47]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]4)[CH2:48][CH2:49]3)=[O:21])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 872981-CyclohexylpiperazineHCID 20468055HCID 20468055, compound

Product 1

HCID 20468144HCID 20468144, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

Into 200 ml of chloroform were added 5.9 g of 1-allyl-6-(3-carboxypropoxy)carbostyril and 3.2 g of DBU. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 2.8 g of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation the reaction mixture was stirred for 1 hour, then 3.7 g of N-cyclohexylpiperazine was added dropwise to the reaction mixture and the reaction was continued for 5 hours. After the reaction was compleated, the reaction mixture was washed with a 1% NaOH aqueous solution and water, then the organic layer was dried with anhydrous Na2SO4. 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 (solvent used was a mixture of chloroform:methanol=30:1) to obtain elute. 4.2 Grams of 1-allyl-6-[3-(4-cyclohexyl-1-piperazinylcarbonyl)propoxy]carbostyril was obtained from the elute, in the form of a colorless oily substance.

Workup

  1. additionThe outside of the reaction vessel containing the
  2. temperaturecooled
  3. stirringAfter the addition operation the reaction mixture was stirred for 1 hour
  4. washthe reaction mixture was washed with a 1% NaOH aqueous solution and water
  5. dry with materialthe organic layer was dried with anhydrous Na2SO4
  6. customThe drying agent was removed by filtration
  7. concentrationthe mother liquor was concentrated
  8. customThe residue thus obtained
  9. additionwas treated by a silica-gel column chromatography (solvent
  10. washelute

Sources & evidence

ORD record
ord-3b445f498e324d108bb44c825b895139
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

Loading…