Hydrochloric Acid → HCID 135621713, compound

HRID 1783318Notes

Reaction equation

HRID 1783318 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:24]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:17](=[O:25])[NH:16][C:15]=3[O:14][N:13]=2)[CH2:8][CH2:7]1)=O)C.COC(N1CCC(C2C3C4C=CC=CC=4C(=O)NC=3ON=2)CC1)=O.[ClH:50]>C(O)(=O)C>[ClH:50].[NH:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:24]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:17](=[O:25])[NH:16][C:15]=3[O:14][N:13]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 135621712HCID 135621712, compoundHCID 135621737HCID 135621737, compound

Product 1

HCID 135621713HCID 135621713, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture (1:1, 2.74 g) of 1-(1-ethoxycarbonylpiperidin-4-yl)-isoxazolo[5,4-c]isoquinolin-5(4H)-one and 1-(1-methoxycarbonylpiperidin-4-yl)-isoxazolo[5,4-c]isoquinolin-5(4H)-one was suspended in acetic acid (15 mL) and concentrated hydrochloric acid (15 mL), and the suspension was heated under reflux for 18 hrs. After the completion of the reaction, the solvent was evaporated. Water and a small amount of methanol were added to the precipitated crystals, and the obtained solution was washed with ethyl acetate, and the aqueous phase was concentrated under reduced pressure. The precipitated crystals were washed with isopropyl alcohol and collected by filtration to give 1-(piperidin-4-yl)-isoxazolo[5,4-c]isoquinolin-5(4H)-one hydrochloride (2.39 g).

Workup

  1. temperatureunder reflux for 18 hrs
  2. customAfter the completion of the reaction
  3. customthe solvent was evaporated
  4. additionWater and a small amount of methanol were added to the precipitated crystals
  5. washthe obtained solution was washed with ethyl acetate
  6. concentrationthe aqueous phase was concentrated under reduced pressure
  7. washThe precipitated crystals were washed with isopropyl alcohol
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c2775f69bc99495c85e29758b94f9ac0
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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