Hydrochloric Acid → HCID 86690341, compound

HRID 1754119Notes

Reaction equation

HRID 1754119 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5]1.[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(O)(C)C.C1(C)C=CC=CC=1.C(O)C>[ClH:1].[F:30][C:16]([F:15])([F:29])[C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][N:4]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]=[CH:5]3)[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 45187433-(2-Chloroethyl)quinazolin-4(3H)-one

Product 1

HCID 86690341HCID 86690341, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

The following were added to a 250 mL reactor: 3-(2-chloroethyl) quinazoline-4(3H)-one (1 g, 4.79 mmol), 1-(3-(trifluoromethyl)phenyl)piperazine (1,103 g, 4.79 mmol), sodium carbonate (0.762 g, 7.19 mmol), sodium iodide (0.072 g, 0.479 mmol), ethanol (50 ml) and toluene (150 ml). The reaction medium was kept under agitation and reflux for a period of twenty hours, during which 150 ml of the solvent were removed slowly with the assistance of a Dean-Stark. To the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate. The mixture was agitated, the organic phase separated, washed with 2 portions of 50 mL of a 5% sodium bicarbonate solution, dry with MgSO4, filtered and evaporated to dryness, yielding the raw product as a slightly yellowish oil. This oil was dissolved in isopropanol, adding 2 mL of concentrated HCl under agitation to the resulting solution. This agitation was maintained for two hours in order to complete the precipitation of the hydrochloride. The resulting solid was filtered and vacuum dried, yielding 1.45 g of 3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4(3H)-one hydrochloride (3.3 mmol, yield=69%).

Workup

  1. additionThe following were added to a 250 mL reactor
  2. customwere removed slowly with the assistance of a Dean-Stark
  3. additionTo the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate
  4. customthe organic phase separated
  5. washwashed with 2 portions of 50 mL of a 5% sodium bicarbonate solution
  6. dry with materialdry with MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customyielding the raw product as a slightly yellowish oil
  10. temperatureThis agitation was maintained for two hours in order
  11. customthe precipitation of the hydrochloride
  12. filtrationThe resulting solid was filtered
  13. customvacuum dried

Sources & evidence

ORD record
ord-e86d929a616748c5bb7242cf38c87025
Source dataset
uspto-grants-2015_10
Patent number
US09169218B2

Reaction notes

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