Potassium Iodide → HCID 12852065, compound

HRID 1248240Notes

Reaction equation

HRID 1248240 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][C:6]1=[O:16].Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8](=[O:15])[NH:7][C:6]3=[O:16])[CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 134765441-(3-Chloropropyl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 12852065HCID 12852065, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.6 parts of 1-(3-chloropropyl)-2,4(1H,3H)-quinazolinedione, 3.02 parts of (4-fluorophenyl)(4-piperidinyl)methanone hydrochloride, 3.7 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight using a water-separator. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and concentrated to a small volume. After cooling the concentrate, the precipitated product is filtered off and crystallized from 2-propanol, yielding 1.3 parts (18.5%) of 1-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2,4(1H,3H)-quinazolinedione; mp. 192.9° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. concentrationconcentrated to a small volume
  7. temperatureAfter cooling the concentrate
  8. filtrationthe precipitated product is filtered off
  9. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-df63f86af4c74c21a3eb66c2ebfc09c7
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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